A theoretical study of new representatives of closed- and open-circle

benzofuran and benzocyclopentadienone oligomersNataliya N. Karausha,*, Gleb V. Baryshnikova,b, Hans Ågrenb,c

and Boris F. Minaeva

a Department of Chemistry and Nanomaterials Science,

Bogdan Khmelnitsky National University, 18031, Cherkasy, UkrainebDivision of Theoretical Chemistry and Biology, School of Engineering Sciences in

Chemistry, Biotechnology and Health, KTH Royal Institute of Technology, 10691

Stockholm, SwedencInstitute of Nanotechnology, Spectroscopy and Quantum Chemistry, Siberian

Federal University, Svobodny pr. 79, 660041 Krasnoyarsk, Russia

Electronic Supplementary Information

List of Content

Bond lengths for selected [n]benzofuran and [n]benzocyclopentadienone systems (Fig. S1–S11) 2Table S1. Total energies of the studied open-circle benzofuran and benzocyclopentadienone oligomers 8Table S2. Total energies of the studied oxa[n]circulenes and [n]circulene ketones 8Table S3. HOMO-LUMO gap for [n]benzofurans and [n]benzocyclopentadienones 9Optimized Cartesian coordinates for selected compounds (Tables S4–S31) 10

1

Electronic Supplementary Material (ESI) for New Journal of Chemistry.This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

Fig. S1. Bond lengths in dibenzofuran calculated at the B3LYP/6-31(d) level of

theory

Fig. S2. Bond lengths in fluoren-9-on calculated at the B3LYP/6-31(d) level of

theory

2

Fig. S3. Bond lengths in the linear benzofuran A9 calculated at the

B3LYP/6-31(d) level of theory

Fig. S4. Bond lengths in the fan-shaped benzofuran B9 calculated at the

B3LYP/6-31(d) level of theory

3

Fig. S5. Bond lengths in the S-shaped benzofuran D9′ calculated at the

B3LYP/6-31(d) level of theory

Fig. S6. Bond lengths in the helical benzofuran D9 calculated at the

B3LYP/6-31(d) level of theory

4

Fig. S7. Bond lengths in the helical benzofuran С9 calculated at the

B3LYP/6-31(d) level of theory

Fig. S8. Bond lengths in the linear benzocyclopentadienone A9 calculated at the

B3LYP/6-31(d) level of theory

5

Fig. S9. Bond lengths in the fan-shaped benzocyclopentadienone B9 calculated at

the B3LYP/6-31(d) level of theory

Fig. S10. Bond lengths in the helical benzocyclopentadienone D9 calculated at the

B3LYP/6-31(d) level of theory

6

Fig. S11. Bond lengths in the helical benzocyclopentadienone С9 calculated at the

B3LYP/6-31(d) level of theory

7

Table S1. Total energies of the studied open-circle benzofuran and benzocyclopentadienone oligomers calculated at the B3LYP/6-31(d) level of theory

Etot, a.u. Etot, a.u. Etot, a.u. Etot, a.u.[n]benzofuran systems

A1 –537.4626A2 –842.4083 B2 –842.4034 C2 –842.6112 D2 –842.6130A3 –1147.4875 B3 –1147.4752 C3 –1147.4737 D3 –1147.4857A4 –1452.5668 B4 –1452.5514 C4 –1452.5429 D4 –1452.5649A5 –1757.6460 B5 –1757.6254 C5 –1757.6096 D5 –1757.6387A6 –2062.7252 B6 –2062.6993 C6 –2062.6771 D6 –2062.7157A7 –2367.8044 B7 –2367.7733 C7 –2367.7440 D7 –2367.7902A8 –2672.8836 B8 –2672.8470 C8 –2672.8105 D8 –2672.8669A9 –2977.9628 B9 –2977.9210 C9 –2977.8770 D9 –2978.6468

[n]benzocyclopentadienone systemsA1 –575.4370A2 –918.6249 B2 –918.6164 C2 –918.6180 D2 –918.6274A3 –1261.8121 B3 –1261.7948 C3 –1261.7933 D3 –1261.8166A4 –1605.3873 B4 –1604.9730 C4 –1604.9697 D4 –1604.9886A5 –1948.1863 B5 –1948.1509 C5 –1948.1452 D5 –1948.1783A6 –2291.3734 B6 –2291.3290 C6 –2291.3203 D6 –2291.3476A7 –2634.5605 B7 –2634.5068 C7 –2634.4952 D7 –2634.5371A8 –2977.7475 B8 –2977.6847 C8 –2977.6698 D8 –2977.7063A9 –3320.9346 B9 –3320.8625 C9 –3320.8445 D9 –3320.8960

Table S2. Total energies of the studied oxa[n]circulenes and [n]circulene ketones calculated at the B3LYP/6-31(d) level of theory

Etot, a.u. n Etot, a.u.oxa[n]circulenes [n]circulene ketones

4 –609.7764 4 –686.03396 –915.0820 6 –1029.46188 –1220.3120 8 –1372.739910 –1525.3038 10 –1715.805112 –1830.2833 12 –2058.932914 –2135.3288 14 –2402.106716 –2440.4037 16 –2745.282018 –2745.4659 18 –3088.397220 –3050.4694 20 –3431.442422 –3355.4095 22 –3774.566624 –3660.3612 24 –4117.746826 –3965.4620 26 –4460.918328 –4270.5420 28 –4804.057130 –4575.5983 30 –5147.1444

8

Table S3. HOMO-LUMO gap for [n]benzofurans and [n]benzocyclopentadienones

calculated at the B3LYP/6-31(d) level of theoryHOMO-LUMO

gap, eVHOMO-LUMO

gap, eVHOMO-LUMO

gap, eVHOMO-LUMO gap,

eV[n]benzofuran systems

A1 4.95A2 4.32 B2 4.52 C2 4.37 D2 4.73A3 3.91 B3 4.23 C3 4.08 D3 4.59A4 3.67 B4 4.04 C4 3.87 D4 4.48A5 3.50 B5 3.93 C5 3.73 D5 4.43A6 3.39 B6 3.84 C6 3.62 D6 4.40A7 3.31 B7 3.79 C7 3.56 D7 4.38A8 3.25 B8 3.74 C8 3.51 D8 4.32A9 3.21 B9 3.71 C9 3.47 D9 4.14

[n]benzocyclopentadienone systemsA1 3.99A2 3.17 B2 3.44 C2 3.45 D2 3.68A3 2.79 B3 3.13 C3 3.23 D3 3.42A4 2.51 B4 2.97 C4 3.14 D4 3.39A5 2.46 B5 2.87 C5 3.09 D5 3.28A6 2.38 B6 2.81 C6 3.06 D6 3.27A7 2.33 B7 2.77 C7 3.06 D7 3.21A8 2.29 B8 2.74 C8 3.05 D8 3.22A9 2.26 B9 2.72 C9 3.02 D9 3.19

9

Table S4. The optimized Cartesian coordinates of the oxa[4]circulene in the

ground singlet state calculated at the B3LYP/6-31(d) level of theory----------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ----------------------------------------------------------- 1 6 0.807697 1.204138 -0.731835 2 6 0.807697 1.204138 0.731835 3 6 -0.671432 1.285107 -0.731835 4 6 -0.671432 1.285107 0.731835 5 6 1.122738 0.042302 1.379954 6 6 1.122738 0.042302 -1.379954 7 6 1.963377 -0.921491 -0.693797 8 6 1.963377 -0.921491 0.693797 9 8 -0.023788 -0.434572 2.078264 10 6 -1.111411 0.164601 1.379954 11 6 -1.111411 0.164601 -1.379954 12 6 -2.052230 -0.701673 -0.693797 13 6 -2.052230 -0.701673 0.693797 14 8 -0.023788 -0.434572 -2.078264 15 1 2.425333 -1.755756 -1.215229 16 1 2.425333 -1.755756 1.215229 17 1 -2.602489 -1.480528 -1.215229 18 1 -2.602489 -1.480528 1.215229 -----------------------------------------------------------

Table S5. The optimized Cartesian coordinates of the oxa[6]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory ----------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ----------------------------------------------------------- 1 6 1.301785 0.550066 -0.880875 2 6 0.191301 1.400229 -0.880897 3 6 1.116983 -0.865786 -0.880897 4 6 -0.174521 -1.402412 -0.880875 5 6 -1.308285 -0.534443 -0.880897 6 6 -1.127264 0.852346 -0.880875 7 6 2.393946 0.817232 -0.065232 8 6 0.164040 2.524167 -0.065117 9 6 2.103972 -1.404146 -0.065117 10 6 -0.489229 -2.481834 -0.065232 11 6 -2.268012 -1.120021 -0.065117 12 6 -1.904716 1.664602 -0.065232 13 6 -3.196090 -0.297334 0.604655 14 6 -3.012824 1.107520 0.604530 15 6 1.340546 2.916562 0.604655 16 6 2.465552 2.055422 0.604530 17 6 0.547272 -3.162942 0.604530 18 6 1.855544 -2.619228 0.604655 19 8 3.010527 -0.392826 0.305640 20 8 -1.165066 2.803606 0.305640 21 8 -1.845461 -2.410780 0.305640 22 1 -3.953328 -0.722708 1.255407 23 1 -3.635693 1.712863 1.255214 24 1 1.350780 3.785037 1.255407 25 1 3.301229 2.292170 1.255214 26 1 0.334463 -4.005034 1.255214 27 1 2.602548 -3.062329 1.255407 -----------------------------------------------------------

10

Table S6. The optimized Cartesian coordinates of the oxa[8]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory --------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z --------------------------------------------------------- 1 6 0.701413 4.166565 0.000000 2 6 -0.701413 4.166565 0.000000 3 6 -1.372083 2.937192 0.000000 4 6 -0.698099 1.710140 0.000000 5 6 0.698099 1.710140 0.000000 6 6 1.372083 2.937192 0.000000 7 8 2.743680 2.743680 0.000000 8 6 2.937192 1.372083 0.000000 9 6 1.710140 0.698099 0.000000 10 6 4.166565 0.701413 0.000000 11 6 4.166565 -0.701413 0.000000 12 1 1.252684 5.100490 0.000000 13 1 -1.252684 5.100490 0.000000 14 1 5.100490 1.252684 0.000000 15 1 5.100490 -1.252684 0.000000 16 6 1.710140 -0.698099 0.000000 17 6 2.937192 -1.372083 0.000000 18 8 2.743680 -2.743680 0.000000 19 6 1.372083 -2.937192 0.000000 20 6 0.698099 -1.710140 0.000000 21 6 0.701413 -4.166565 0.000000 22 6 -0.701413 -4.166565 0.000000 23 1 1.252684 -5.100490 0.000000 24 1 -1.252684 -5.100490 0.000000 25 6 -0.698099 -1.710140 0.000000 26 6 -1.372083 -2.937192 0.000000 27 8 -2.743680 -2.743680 0.000000 28 6 -2.937192 -1.372083 0.000000 29 6 -1.710140 -0.698099 0.000000 30 6 -4.166565 -0.701413 0.000000 31 6 -4.166565 0.701413 0.000000 32 6 -2.937192 1.372083 0.000000 33 6 -1.710140 0.698099 0.000000 34 1 -5.100490 -1.252684 0.000000 35 1 -5.100490 1.252684 0.000000 36 8 -2.743680 2.743680 0.000000 ---------------------------------------------------------

Table S7. The optimized Cartesian coordinates of the oxa[10]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 0.725059 -0.157754 -2.206279 2 6 1.881594 -0.193089 -1.339108 3 6 2.312084 0.233475 0.013689 4 6 1.801994 0.593810 1.315692 5 6 -0.725059 0.157754 -2.206279 6 6 -1.881594 0.193089 -1.339108 7 6 -0.644200 -0.324569 2.197262 8 6 -2.312084 -0.233475 0.013689 9 6 -1.801994 -0.593810 1.315692 10 6 0.644200 0.324569 2.197262 11 6 -2.769825 -1.164436 2.186848

11

12 8 -2.307069 -1.327458 3.453147 13 6 -1.093888 -0.720605 3.485175 14 6 -0.555054 -0.405132 4.730776 15 6 0.555054 0.405132 4.730776 16 6 1.093888 0.720605 3.485175 17 8 2.307069 1.327458 3.453147 18 6 2.769825 1.164436 2.186848 19 6 4.131396 1.364042 1.970969 20 6 4.643236 0.851822 0.803192 21 6 3.729505 0.282574 -0.079661 22 6 -3.729505 -0.282574 -0.079661 23 6 -4.643236 -0.851822 0.803192 24 6 -4.131396 -1.364042 1.970969 25 6 -3.104428 0.478623 -2.009303 26 8 -4.196635 0.229263 -1.243998 27 6 -3.318533 0.816374 -3.342047 28 6 -2.232024 0.711602 -4.176275 29 6 -1.035222 0.319397 -3.585729 30 8 0.000000 0.000000 -4.399440 31 6 1.035222 -0.319397 -3.585729 32 6 2.232024 -0.711602 -4.176275 33 6 3.318533 -0.816374 -3.342047 34 6 3.104428 -0.478623 -2.009303 35 8 4.196635 -0.229263 -1.243998 36 1 -1.049739 -0.743289 5.633989 37 1 1.049739 0.743289 5.633989 38 1 4.742713 1.805258 2.749737 39 1 5.696966 0.873203 0.550089 40 1 -5.696966 -0.873203 0.550089 41 1 -4.742713 -1.805258 2.749737 42 1 -4.321039 1.038533 -3.689180 43 1 -2.284195 0.853589 -5.249581 44 1 2.284195 -0.853589 -5.249581 45 1 4.321039 -1.038533 -3.689180 --------------------------------------------------------

Table S8. The optimized Cartesian coordinates of the oxa[12]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 2.246534 -0.345688 0.933092 2 6 1.974873 1.064613 0.981162 3 6 -2.044941 1.418528 -0.044737 4 6 -2.246294 0.345671 0.933297 5 6 -1.974668 -1.064628 0.981280 6 6 2.045089 -1.418561 -0.044925 7 6 1.075452 -1.915613 -0.978333 8 6 -0.371659 -2.188256 -0.931177 9 6 -1.408582 -2.044705 0.049489 10 6 -1.075393 1.915597 -0.978224 11 6 0.371707 2.188339 -0.931108 12 6 1.408720 2.044758 0.049455 13 6 2.857582 1.818860 1.791990 14 6 3.766966 1.322771 2.726554 15 6 4.038690 -0.032834 2.668800 16 6 3.369282 -0.764417 1.687883 17 8 3.934990 -1.901674 1.178293 18 6 3.212808 -2.206229 0.060444 19 6 2.200657 3.198379 0.237627 20 8 2.959726 3.117479 1.369854

12

21 6 0.559796 3.238668 -1.855520 22 6 1.552393 4.225041 -1.799667 23 6 2.344840 4.253624 -0.666766 24 6 -1.572716 2.826262 -1.936254 25 8 -0.565564 3.477534 -2.600805 26 6 -2.861328 3.372582 -1.973409 27 6 -3.681620 3.115408 -0.890153 28 6 -3.212785 2.205997 0.060524 29 8 -3.934885 1.901530 1.178444 30 6 -3.369047 0.764365 1.688100 31 6 -4.038409 0.032748 2.669023 32 6 -3.766732 -1.322866 2.726661 33 6 -2.857419 -1.818914 1.792013 34 6 -2.200779 -3.198187 0.237350 35 8 -2.959776 -3.117428 1.369616 36 6 -2.345176 -4.253178 -0.667330 37 6 -0.559961 -3.238298 -1.855873 38 6 -1.552748 -4.224465 -1.800242 39 8 0.565393 -3.477292 -2.601079 40 6 1.572635 -2.826445 -1.936226 41 6 3.681461 -3.115925 -0.890034 42 6 2.861112 -3.373147 -1.973222 43 1 4.348150 2.002664 3.339524 44 1 4.845244 -0.485185 3.235021 45 1 1.571772 5.015227 -2.541845 46 1 3.060235 5.045252 -0.474360 47 1 -3.120023 4.096847 -2.737738 48 1 -4.646555 3.592901 -0.762160 49 1 -4.844969 0.485065 3.235259 50 1 -4.347956 -2.002790 3.339558 51 1 -3.060709 -5.044726 -0.475117 52 1 -1.572285 -5.014484 -2.542594 53 1 4.646317 -3.593557 -0.761953 54 1 3.119683 -4.097535 -2.737474 --------------------------------------------------------

Table S9. The optimized Cartesian coordinates of the oxa[14]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 1.499899 1.098400 -1.544440 2 6 2.197097 -0.091718 -1.164407 3 6 -0.501613 -2.410168 0.614117 4 6 -0.961984 -2.214987 -0.750130 5 6 -1.448629 -1.133178 -1.546298 6 6 0.954077 2.191241 -0.742023 7 6 0.499408 2.393427 0.592405 8 6 -0.495496 1.837563 1.504968 9 6 -2.150230 0.098573 -1.176210 10 6 0.437825 -1.817993 1.511395 11 6 1.724854 -1.157531 1.275915 12 6 2.432676 -0.767803 0.101782 13 6 3.311297 -0.426344 -1.963673 14 6 1.919079 1.706398 -2.746695 15 8 1.681118 3.063012 -2.741720 16 6 1.287537 3.355651 -1.457816 17 6 3.771750 -1.198401 0.034063 18 8 4.262586 -1.109817 -1.243766 19 6 2.513468 -1.508605 2.387422 20 6 0.576011 -2.438182 2.768501

13

21 8 1.761401 -2.095127 3.380295 22 6 -0.909680 -3.717886 0.947387 23 8 -1.349347 -4.403466 -0.156901 24 6 -1.331939 -3.502131 -1.192022 25 6 -1.960165 -1.473048 -2.814570 26 6 -3.075130 0.305878 -2.216267 27 8 -2.816131 -0.507177 -3.296118 28 6 -0.423857 2.649916 2.656939 29 8 0.495507 3.664203 2.507832 30 6 0.896957 3.600876 1.195588 31 6 -2.434598 0.757136 0.054856 32 6 -3.779198 1.128908 0.244693 33 6 -1.754452 1.201922 1.262531 34 6 -2.793145 1.541987 2.156143 35 8 -4.026241 1.466779 1.551166 36 6 -4.323409 0.925584 -2.067106 37 6 -4.719341 1.271170 -0.781024 38 6 -2.625496 2.148929 3.402255 39 6 -1.384127 2.711358 3.670873 40 6 1.387770 4.713775 0.502254 41 6 1.501101 4.613068 -0.879318 42 6 3.564110 0.062805 -3.246627 43 6 2.818966 1.157313 -3.665931 44 6 3.906781 -1.661433 2.367410 45 6 4.543236 -1.582066 1.135317 46 6 -0.828533 -4.284046 2.221881 47 6 -0.111690 -3.586212 3.184714 48 6 -2.005677 -2.766649 -3.350843 49 6 -1.735453 -3.822155 -2.490198 50 1 -5.001860 0.991719 -2.910518 51 1 -5.712497 1.651161 -0.568841 52 1 -3.475245 2.309793 4.056552 53 1 -1.222359 3.336697 4.542055 54 1 1.594172 5.639081 1.028629 55 1 1.834328 5.445527 -1.489120 56 1 4.404399 -0.307475 -3.823540 57 1 3.057353 1.687240 -4.581655 58 1 4.430580 -1.985548 3.259952 59 1 5.596364 -1.811942 1.017683 60 1 -1.250431 -5.262995 2.420564 61 1 0.073240 -4.003682 4.168433 62 1 -2.425059 -2.932156 -4.337219 63 1 -1.914477 -4.852704 -2.776136 --------------------------------------------------------

Table S10. The optimized Cartesian coordinates of the oxa[16]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 1.010530 -1.737294 -1.604297 2 6 -0.376089 -2.050982 -1.606467 3 6 1.840379 0.540766 1.509644 4 6 1.010545 1.737286 1.604292 5 6 -0.376071 2.050984 1.606463 6 6 1.576826 0.842604 -1.751062 7 6 0.376029 1.606496 -2.050828 8 6 -1.010607 1.604418 -1.737230 9 6 -1.576918 1.751301 0.842630 10 6 0.376023 -1.606502 2.050829 11 6 -1.010613 -1.604416 1.737232

14

12 6 -1.840493 -1.509864 0.540748 13 6 -0.782064 -3.014650 -2.549392 14 6 1.865303 -2.723871 -2.130505 15 6 -3.150225 -1.790825 0.985504 16 6 -1.865310 -2.130731 2.723827 17 6 0.782101 -2.549477 3.014415 18 6 3.150146 0.985489 1.790488 19 8 3.182489 2.334111 2.066300 20 6 1.865326 2.723858 2.130494 21 6 -0.782036 3.014658 2.549387 22 6 -2.627597 2.344372 1.575706 23 8 -2.151818 3.080923 2.636449 24 6 -1.865302 2.130747 -2.723820 25 6 0.782114 2.549474 -3.014410 26 8 -3.182491 -2.066662 2.334124 27 8 2.151904 2.636498 -3.080530 28 6 -3.150217 1.790842 -0.985498 29 8 -3.182484 2.066684 -2.334117 30 6 -1.840486 1.509871 -0.540746 31 6 1.840372 -0.540780 -1.509645 32 8 3.182468 -2.334132 -2.066316 33 6 3.150136 -0.985511 -1.790496 34 6 1.576824 -0.842616 1.751063 35 6 2.627565 -1.575699 2.344010 36 8 2.151891 -2.636513 3.080533 37 6 -1.576931 -1.751294 -0.842628 38 6 -2.627616 -2.344357 -1.575702 39 8 -2.151846 -3.080908 -2.636449 40 6 3.959723 -1.165476 2.412748 41 6 4.234072 0.162910 2.106684 42 6 1.439573 3.816951 2.894255 43 6 -3.959736 2.413249 1.165450 44 6 -4.234104 2.107162 -0.162933 45 6 -0.080834 3.181935 -3.914793 46 6 4.234067 -0.162938 -2.106689 47 6 3.959727 1.165451 -2.412746 48 6 0.080989 -3.914982 -3.181798 49 6 -4.234117 -2.107138 0.162943 50 6 -3.959754 -2.413228 -1.165441 51 6 -1.439426 -2.894484 3.816871 52 6 -0.080850 -3.181929 3.914802 53 1 4.717587 -1.820054 2.828925 54 1 5.215689 0.591578 2.276463 55 1 -4.717569 2.829556 1.819982 56 1 -5.215697 2.277061 -0.591610 57 1 0.311119 3.834703 -4.686881 58 1 5.215681 -0.591612 -2.276470 59 1 4.717596 1.820027 -2.828919 60 1 -5.215709 -2.277030 0.591623 61 1 -4.717593 -2.829530 -1.819970 62 1 -2.164509 -3.327725 4.496958 63 1 0.311099 -3.834697 4.686891 64 6 1.439540 -3.816956 -2.894272 65 6 -1.439412 2.894502 -3.816861 66 1 -2.164492 3.327751 -4.496946 67 6 0.081024 3.914988 3.181785 68 1 2.164740 4.497011 3.327397 69 1 -0.310836 4.687144 3.834526 70 1 -0.310878 -4.687132 -3.834542 71 1 2.164700 -4.497019 -3.327421 72 6 2.627572 1.575681 -2.344008 --------------------------------------------------------

15

Table S11. The optimized Cartesian coordinates of the oxa[18]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory --------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z --------------------------------------------------------- 1 6 -0.729474 0.012766 2.726912 2 6 0.729474 -0.012766 2.726912 3 6 -1.839644 -0.395815 -1.878882 4 6 -0.715061 -0.015096 -2.738750 5 6 0.715061 0.015096 -2.738750 6 6 -2.080932 1.328221 0.780637 7 6 -1.374437 2.389562 0.124125 8 6 0.000000 2.870193 0.000632 9 6 1.839644 0.395815 -1.878882 10 6 0.000000 -2.870193 0.000632 11 6 1.374437 -2.389562 0.124125 12 6 2.080932 -1.328221 0.780637 13 6 1.080035 0.165304 4.086035 14 6 -1.080035 -0.165304 4.086035 15 6 -3.491902 1.418679 0.724776 16 6 3.491902 -1.418679 0.724776 17 6 2.165724 -3.515164 -0.216580 18 6 0.124552 -4.276313 -0.056300 19 8 1.414656 -4.657032 -0.310165 20 6 -2.985471 -0.026405 -2.627628 21 8 -2.663346 0.409117 -3.885110 22 6 -1.307322 0.263366 -3.990152 23 6 1.307322 -0.263366 -3.990152 24 6 2.985471 0.026405 -2.627628 25 8 2.663346 -0.409117 -3.885110 26 6 -0.124552 4.276313 -0.056300 27 8 -1.414656 4.657032 -0.310165 28 6 -2.165724 3.515164 -0.216580 29 8 0.000000 0.000000 4.911762 30 6 2.334536 3.306368 0.287425 31 6 -1.819624 0.364036 1.866642 32 6 -3.100800 0.043277 2.369192 33 8 -4.103763 0.547945 1.586263 34 6 -1.341165 -2.385307 -0.110644 35 6 -2.334536 -3.306368 0.287425 36 6 1.819624 -0.364036 1.866642 37 6 3.100800 -0.043277 2.369192 38 8 4.103763 -0.547945 1.586263 39 6 -3.443941 -1.642364 -0.576196 40 8 -3.592951 -2.782874 0.165644 41 6 -2.082588 -1.319784 -0.803033 42 6 3.443941 1.642364 -0.576196 43 8 3.592951 2.782874 0.165644 44 6 2.082588 1.319784 -0.803033 45 6 1.341165 2.385307 -0.110644 46 6 -4.554758 -1.077412 -1.200362 47 6 -4.316595 -0.245926 -2.280775 48 6 -0.668099 0.185544 -5.230319 49 6 0.668099 -0.185544 -5.230319 50 6 -0.890015 -5.193311 0.222280 51 6 -2.148126 -4.676991 0.493310 52 6 4.240121 -2.427498 0.117176 53 6 3.552765 -3.544485 -0.329739 54 6 2.353469 0.464593 4.567106 55 6 3.393515 0.430846 3.651443 56 6 -3.393515 -0.430846 3.651443 57 6 -2.353469 -0.464593 4.567106

16

58 6 -3.552765 3.544485 -0.329739 59 6 -4.240121 2.427498 0.117176 60 6 2.148126 4.676991 0.493310 61 6 0.890015 5.193311 0.222280 62 6 4.316595 0.245926 -2.280775 63 6 4.554758 1.077412 -1.200362 64 1 -5.553182 -1.393468 -0.920111 65 1 -5.114520 0.126409 -2.913447 66 1 -1.230051 0.335080 -6.145393 67 1 1.230051 -0.335080 -6.145393 68 1 -0.680346 -6.256808 0.244877 69 1 -2.995115 -5.310073 0.732916 70 1 5.323212 -2.387998 0.143336 71 1 4.059487 -4.440443 -0.670303 72 1 2.511592 0.676513 5.618574 73 1 4.423206 0.610745 3.939463 74 1 -4.423206 -0.610745 3.939463 75 1 -2.511592 -0.676513 5.618574 76 1 -4.059487 4.440443 -0.670303 77 1 -5.323212 2.387998 0.143336 78 1 2.995115 5.310073 0.732916 79 1 0.680346 6.256808 0.244877 80 1 5.114520 -0.126409 -2.913447 81 1 5.553182 1.393468 -0.920111 ---------------------------------------------------------

Table S12. The optimized Cartesian coordinates of the oxa[20]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory ------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 0.325320 2.835042 -1.070872 2 6 0.404093 3.051739 0.388161 3 6 -0.617839 -1.847752 -2.091666 4 6 -0.325320 -2.835042 -1.070872 5 6 -0.199328 -2.401605 1.666856 6 6 1.458742 0.631352 -2.335207 7 6 2.445246 -0.218651 -1.689278 8 6 3.090225 -0.414406 -0.374198 9 6 0.695359 -1.411836 2.343721 10 6 -2.869791 0.286402 1.047351 11 6 -1.875552 0.588874 2.109835 12 6 -0.695359 1.411836 2.343721 13 6 0.660911 4.443913 0.500228 14 6 0.130633 4.148925 -1.583432 15 6 1.434235 0.489530 -3.749360 16 6 -0.383568 1.586053 3.721194 17 6 -2.540000 0.161834 3.298208 18 6 -4.049599 -0.044277 1.757109 19 8 -3.807446 -0.278052 3.073300 20 6 -0.247681 -2.270368 -3.396454 21 6 -0.130633 -4.148925 -1.583432 22 6 -0.822898 -3.091861 2.737641 23 6 0.383568 -1.586053 3.721194 24 8 -0.585521 -2.510183 3.941748 25 6 4.409201 -0.818319 -0.697967 26 8 4.513943 -1.225396 -1.991154 27 6 3.345282 -0.861688 -2.587530 28 8 0.389593 5.110200 -0.654645 29 6 4.049599 0.044277 1.757109 30 6 0.617839 1.847752 -2.091666

17

31 6 0.247681 2.270368 -3.396454 32 8 0.643294 1.404114 -4.364382 33 6 -3.090225 0.414406 -0.374198 34 6 -4.409201 0.818319 -0.697967 35 6 0.199328 2.401605 1.666856 36 6 0.822898 3.091861 2.737641 37 8 0.585521 2.510183 3.941748 38 6 -3.345282 0.861688 -2.587530 39 8 -4.513943 1.225396 -1.991154 40 6 -2.445246 0.218651 -1.689278 41 6 2.540000 -0.161834 3.298208 42 8 3.807446 0.278052 3.073300 43 6 1.875552 -0.588874 2.109835 44 6 2.869791 -0.286402 1.047351 45 6 -5.371977 0.100192 1.328704 46 6 -5.555200 0.660622 0.082428 47 6 -1.022245 1.064987 4.842817 48 6 -2.153525 0.318837 4.623926 49 6 1.201506 5.118707 1.591678 50 6 1.377277 4.374384 2.737501 51 6 -0.247681 3.506780 -3.808431 52 6 -0.241031 4.516005 -2.871077 53 6 3.226556 -1.026579 -3.962557 54 6 2.202181 -0.337266 -4.566217 55 6 5.371977 -0.100192 1.328704 56 6 5.555200 -0.660622 0.082428 57 6 1.022245 -1.064987 4.842817 58 6 2.153525 -0.318837 4.623926 59 1 -6.187324 -0.113767 2.010168 60 1 -6.529183 0.914613 -0.319873 61 1 -0.659451 1.323614 5.830484 62 1 -2.783995 -0.062052 5.418883 63 1 1.459224 6.168853 1.515715 64 1 1.778516 4.785391 3.656765 65 1 -0.474379 3.671334 -4.855417 66 1 -0.455956 5.551946 -3.106971 67 1 3.968417 -1.596341 -4.510289 68 1 2.036376 -0.331649 -5.637046 69 1 6.187324 0.113767 2.010168 70 1 6.529183 -0.914613 -0.319873 71 1 0.659451 -1.323614 5.830484 72 1 2.783995 0.062052 5.418883 73 6 -0.404093 -3.051739 0.388161 74 6 -0.660911 -4.443913 0.500228 75 8 -0.389593 -5.110200 -0.654645 76 6 -1.458742 -0.631352 -2.335207 77 6 -1.434235 -0.489530 -3.749360 78 8 -0.643294 -1.404114 -4.364382 79 6 -2.202181 0.337266 -4.566217 80 6 -3.226556 1.026579 -3.962557 81 1 -2.036376 0.331649 -5.637046 82 1 -3.968417 1.596341 -4.510289 83 6 -1.377277 -4.374384 2.737501 84 6 -1.201506 -5.118707 1.591678 85 6 0.241031 -4.516005 -2.871077 86 6 0.247681 -3.506780 -3.808431 87 1 -1.778516 -4.785391 3.656765 88 1 -1.459224 -6.168853 1.515715 89 1 0.455956 -5.551946 -3.106971 90 1 0.474379 -3.671334 -4.855417 -------------------------------------------------------

18

Table S13. The optimized Cartesian coordinates of the oxa[22]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 -0.728595 -3.272354 0.130759 2 6 0.724524 -3.247905 0.433278 3 6 -2.598719 1.365953 -0.945801 4 6 -0.712094 3.267001 -0.120818 5 6 2.597935 1.512699 0.691565 6 6 -2.616871 -1.328332 0.918064 7 6 -2.420233 -0.258421 1.920209 8 6 -1.416366 0.374207 2.857351 9 6 2.372813 0.589664 1.889612 10 6 1.421395 -0.130385 -2.878541 11 6 2.423127 -0.590496 -1.843719 12 6 2.616690 -1.469869 -0.670717 13 6 0.977778 -4.587404 0.849300 14 6 -0.983579 -4.662639 -0.053484 15 6 -3.991467 -1.518924 0.580663 16 6 3.990202 -1.599967 -0.301818 17 6 3.652758 -0.096780 -2.379259 18 6 2.224863 0.423428 -3.908803 19 8 3.516051 0.578667 -3.541043 20 6 -4.014744 1.356479 -0.784499 21 6 -1.136520 4.565876 0.249991 22 6 4.013497 1.477239 0.530761 23 6 3.693725 0.167649 2.220178 24 8 4.639881 0.654029 1.393674 25 6 -2.217566 1.101015 3.775734 26 8 -3.508860 1.192335 3.387566 27 6 -3.648148 0.323793 2.362320 28 8 -0.003387 -5.443139 0.467231 29 6 0.047136 0.301962 4.739442 30 6 -1.948288 -2.470622 0.172027 31 6 -3.024987 -3.137836 -0.472463 32 8 -4.209621 -2.509623 -0.310155 33 6 0.035083 -0.295089 -3.320851 34 6 -0.040773 -0.526716 -4.720529 35 6 1.945331 -2.466193 0.258995 36 6 3.019858 -3.014438 1.010260 37 8 4.205383 -2.423600 0.745926 38 6 -2.008916 -1.029244 -3.993967 39 8 -1.208366 -1.103756 -5.085554 40 6 -1.396626 -0.353564 -2.891793 41 6 2.015310 -0.317576 4.109677 42 8 1.215298 -0.202492 5.198255 43 6 1.401410 0.155930 2.907575 44 6 -0.029883 0.287000 3.320973 45 6 1.969770 0.527269 -5.281273 46 6 0.829529 -0.092869 -5.720386 47 6 5.147875 -1.108733 -0.895848 48 6 4.970314 -0.317087 -1.990605 49 6 2.051569 -5.074849 1.583959 50 6 3.095027 -4.198683 1.747040 51 6 -3.102380 -4.429010 -0.999218 52 6 -2.058870 -5.266053 -0.693576 53 6 -4.966865 0.039261 2.022438 54 6 -5.147559 -0.931720 1.083765 55 6 -0.821740 0.904946 5.648996 56 6 -1.960869 1.441809 5.109003 57 6 4.183823 -0.557287 3.304861

19

58 6 3.306152 -0.778204 4.329594 59 1 2.734129 0.925855 -5.938028 60 1 0.567610 -0.220779 -6.764251 61 1 6.112031 -1.377580 -0.481679 62 1 5.775517 0.108365 -2.577417 63 1 2.051060 -6.094643 1.951055 64 1 4.020054 -4.452885 2.251239 65 1 -4.028684 -4.763125 -1.451786 66 1 -2.059570 -6.333084 -0.883767 67 1 -5.770252 0.561644 2.527790 68 1 -6.112929 -1.267992 0.725411 69 1 -0.559372 0.960199 6.699107 70 1 -2.723850 1.950319 5.686707 71 1 5.237663 -0.805819 3.341427 72 1 3.579761 -1.198378 5.290399 73 6 0.706463 3.241395 -0.441699 74 6 1.127970 4.459991 -1.026514 75 6 -2.369842 0.249019 -1.965182 76 6 -3.689309 -0.227482 -2.218372 77 8 -4.637857 0.393639 -1.491114 78 6 -4.177106 -1.131275 -3.160389 79 6 -3.298534 -1.524185 -4.131291 80 1 -5.230440 -1.384459 -3.153184 81 1 -3.570434 -2.105146 -5.004853 82 6 1.974520 2.484463 -0.223801 83 6 2.909609 3.243030 -1.000303 84 8 2.385703 4.382268 -1.519070 85 6 -1.978493 2.481335 -0.208972 86 6 -2.916424 3.358792 0.426127 87 8 -2.395017 4.569984 0.746505 88 6 4.862649 2.179002 -0.321280 89 6 4.284302 3.109232 -1.136179 90 6 0.553543 5.728986 -0.890500 91 6 -0.563783 5.795090 -0.096200 92 6 -4.291722 3.249310 0.577512 93 6 -4.867090 2.193239 -0.068668 94 1 5.929198 1.999191 -0.265922 95 1 4.833196 3.784054 -1.782283 96 1 1.056162 6.596686 -1.301728 97 1 -1.067814 6.718650 0.163837 98 1 -4.842901 4.023869 1.097497 99 1 -5.933355 2.005363 -0.095626 --------------------------------------------------------

Table S14. The optimized Cartesian coordinates of the oxa[24]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory -------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 8 3.291043 -3.319643 2.470491 2 6 1.551540 -0.895127 4.563950 3 6 -1.630149 -2.975204 -0.085447 4 6 -1.439901 -2.417129 -1.382546 5 6 -1.891957 -1.187590 -2.055831 6 6 5.907529 0.405094 -0.941054 7 6 5.925486 0.244852 0.441370 8 6 3.466988 1.374326 2.581544 9 6 2.701576 1.353285 1.397926 10 8 4.614815 0.611874 2.465451 11 6 4.697725 0.307603 1.123800 12 6 3.461694 0.485581 0.488466

20

13 6 3.444389 0.186974 -0.904933 14 6 4.656869 0.396065 -1.578531 15 1 6.822162 0.464089 -1.520632 16 1 6.855941 0.205424 0.997130 17 6 -2.559847 3.916643 1.331469 18 6 -2.017283 2.730505 0.798302 19 6 -2.935795 4.098962 2.667429 20 6 -3.083667 2.958221 3.440569 21 6 -2.995317 1.723845 2.770570 22 6 -2.466563 1.539615 1.479780 23 1 -3.214157 5.079176 3.038600 24 1 -3.501466 3.005151 4.440404 25 8 -3.947807 0.768573 3.079507 26 6 -4.264121 0.196818 1.864383 27 6 -3.265122 0.438776 0.910108 28 6 -3.582636 0.056439 -0.426398 29 6 -4.953193 0.073495 -0.738263 30 6 -5.971201 -0.084252 0.210075 31 6 -5.595353 -0.125893 1.549396 32 1 -6.330411 -0.222963 2.340901 33 1 -7.008045 -0.170983 -0.095206 34 8 -5.146854 0.163455 -2.097679 35 6 -3.905583 -0.030401 -2.664370 36 6 -2.923208 -0.262534 -1.679543 37 6 -1.797960 -1.478733 -3.430545 38 6 -2.581258 -0.895192 -4.437403 39 6 -3.711306 -0.192511 -4.038152 40 1 -4.476086 0.102645 -4.748113 41 1 -2.433035 -1.179291 -5.473637 42 6 -1.258920 -3.342604 -2.425198 43 8 -1.245181 -2.724127 -3.655949 44 6 -2.122199 -4.295951 -0.064013 45 6 -1.981698 -5.205708 -1.114270 46 6 -1.452198 -4.725319 -2.308659 47 1 -1.338125 -5.363486 -3.177737 48 1 -2.303634 -6.235480 -1.005857 49 8 -2.769376 -4.562817 1.121092 50 6 -2.581376 -3.450221 1.909741 51 6 -1.717321 -2.526093 1.288369 52 6 -1.030600 -1.639785 2.171993 53 6 -1.641571 -1.438024 3.423173 54 6 -2.732707 -2.170900 3.910802 55 6 -3.161738 -3.264877 3.166482 56 1 -3.890122 -3.969081 3.553020 57 1 -3.109570 -1.978805 4.909043 58 8 -0.823749 -0.741855 4.283887 59 6 0.432570 -0.828712 3.722429 60 6 0.384682 -1.289546 2.391102 61 6 2.621844 -1.677680 4.147409 62 6 2.545830 -2.231561 2.868541 63 6 1.596402 -1.870122 1.889032 64 1 3.435489 -1.933764 4.816741 65 1 1.485102 -0.525579 5.581473 66 6 2.833161 -3.645617 1.214000 67 6 1.968025 -2.650603 0.723343 68 6 3.092981 -4.849590 0.550973 69 6 2.527642 -5.023581 -0.711416 70 6 1.906433 -3.916290 -1.305809 71 6 1.762952 -2.666278 -0.682517 72 8 1.693335 -3.823324 -2.664082 73 6 1.760577 -2.475876 -2.948811 74 6 1.833295 -1.695417 -1.777088 75 6 2.125660 -2.049921 -4.231719

21

76 6 2.918896 -0.913865 -4.317603 77 6 3.247995 -0.277416 -3.116404 78 6 2.593261 -0.478386 -1.883366 79 8 4.483762 0.313451 -2.941785 80 1 1.971592 -2.697057 -5.088010 81 1 3.415713 -0.641582 -5.242483 82 1 2.675198 -5.936632 -1.277715 83 1 3.693884 -5.622217 1.017590 84 6 1.623427 3.165448 -0.216034 85 6 2.198908 4.445385 -0.188776 86 6 2.009633 2.578686 1.066304 87 6 2.396030 3.684314 1.853698 88 6 2.927706 3.615813 3.145725 89 6 3.446922 2.393862 3.545634 90 8 2.507891 4.827427 1.092529 91 1 3.086629 4.516423 3.728797 92 1 4.036283 2.303024 4.451603 93 6 -1.678185 3.073282 -0.578673 94 6 -2.416262 4.244969 -0.828251 95 6 -0.888066 3.369308 -2.833721 96 6 -1.964946 4.220842 -3.159845 97 6 -2.682248 4.758840 -2.104707 98 1 -3.380536 5.577056 -2.241583 99 1 -2.044702 4.625128 -4.163127 100 6 -0.649353 2.821345 -1.562554 101 6 0.826400 2.916406 -1.393177 102 6 2.188046 4.642286 -2.561832 103 6 2.569209 5.165222 -1.337315 104 1 2.407231 5.153850 -3.492637 105 1 3.142187 6.082126 -1.254825 106 6 1.255761 3.580714 -2.550512 107 8 -2.852240 4.821299 0.338684 108 8 0.286743 3.571559 -3.535817 --------------------------------------------------------

Table S15. The optimized Cartesian coordinates of the oxa[26]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory ------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 2.716459 1.036029 1.628727 2 6 3.473837 0.815676 0.405337 3 6 -0.854060 -2.996132 1.332908 4 6 -0.930538 -2.972731 -1.368955 5 6 -3.415419 -0.714859 -0.731305 6 6 1.092926 3.356725 -0.282522 7 6 -0.607355 2.267343 -2.003594 8 6 -1.937003 2.375449 -1.384792 9 6 -3.409978 -0.752673 0.718134 10 6 2.376196 -2.488765 -0.724393 11 6 2.161360 -1.530939 -1.805178 12 6 2.506222 -0.136866 -1.916915 13 6 4.818672 0.906320 0.798521 14 6 3.664225 0.878455 2.662428 15 6 1.665966 4.600123 -0.595993 16 6 2.902176 0.297023 -3.200684 17 6 2.314879 -2.292387 -2.984130 18 6 2.936930 -3.613091 -1.351465 19 8 2.710965 -3.584138 -2.709825 20 6 -1.579179 -3.697222 2.310302 21 6 -0.820177 -4.144793 -2.148284

22

22 6 -4.777429 -0.805599 -1.082434 23 6 -4.682609 -1.248221 1.065403 24 8 -5.540008 -1.210233 -0.010473 25 6 -2.797895 2.689206 -2.448019 26 8 -2.207244 2.426717 -3.665724 27 6 -0.856622 2.335407 -3.389344 28 8 4.943045 0.747802 2.161212 29 6 -2.656325 3.462307 2.029418 30 6 1.097139 3.025010 1.102740 31 6 1.027911 4.112170 1.985969 32 6 2.430878 -2.492499 0.697073 33 6 3.521621 -3.182790 1.251934 34 6 3.253066 0.721213 -0.997109 35 6 4.215069 1.351135 -1.800882 36 8 3.869316 1.280481 -3.132556 37 6 2.428106 -2.348202 2.957828 38 8 3.623790 -2.934240 2.602369 39 6 1.593173 -2.145501 1.837690 40 6 -2.051598 1.269682 3.443223 41 6 -2.066311 1.133492 2.041591 42 6 -2.181120 2.353884 1.298875 43 6 3.859582 -4.470083 -0.734516 44 6 4.238133 -4.178771 0.575186 45 6 2.719438 -0.416841 -4.389453 46 6 2.425352 -1.769443 -4.275416 47 6 5.844601 1.353415 -0.045779 48 6 5.503946 1.684845 -1.356118 49 1 4.331837 -5.266590 -1.298917 50 1 5.007342 -4.748061 1.085249 51 1 3.007739 0.018014 -5.340215 52 1 2.469177 -2.429892 -5.134271 53 1 6.848927 1.500926 0.335716 54 1 6.236717 2.081853 -2.050012 55 6 -1.381170 -1.807793 -2.076467 56 6 -1.300255 -1.876230 -3.481993 57 6 0.181903 -2.277690 2.085589 58 6 -0.188342 -2.441146 3.437982 59 8 -1.331514 -3.200477 3.570264 60 6 0.658854 -2.281205 4.540848 61 6 2.024331 -2.263243 4.292061 62 1 0.269392 -2.386593 5.547460 63 1 2.747798 -2.347897 5.095387 64 6 -2.499838 -0.881825 -1.816310 65 6 -3.010293 -0.580819 -3.092235 66 8 -2.154278 -0.982978 -4.092610 67 6 -1.025501 -3.456925 -0.003161 68 6 -1.342805 -4.822091 -0.127577 69 8 -1.083664 -5.271844 -1.401916 70 6 -5.283057 -0.533891 -2.356310 71 6 -4.360453 -0.327983 -3.376370 72 6 -0.835201 -2.975896 -4.215938 73 6 -0.647639 -4.171132 -3.532879 74 6 -1.953527 -5.577388 0.879401 75 6 -2.166721 -4.954543 2.106894 76 1 -6.351547 -0.524016 -2.540925 77 1 -4.673753 -0.155543 -4.400061 78 1 -0.834381 -2.939102 -5.299899 79 1 -0.480896 -5.106768 -4.054817 80 1 -2.265850 -6.599326 0.695368 81 1 -2.643900 -5.472670 2.931441 82 6 -2.416973 2.704775 -0.086607 83 6 -3.328199 3.775995 -0.037721 84 8 -3.378362 4.318643 1.227069

23

85 6 -2.663505 -0.194768 1.802201 86 6 -3.012677 -0.655983 3.083699 87 6 -5.035729 -1.689603 2.343366 88 6 -4.126181 -1.459756 3.369856 89 6 -2.160075 2.483934 4.137976 90 6 -2.543513 3.606366 3.413576 91 6 -3.916004 3.529073 -2.335896 92 6 -4.127893 4.168194 -1.115680 93 1 -5.999729 -2.151037 2.526738 94 1 -4.347051 -1.731329 4.396066 95 1 -2.158530 2.487898 5.222552 96 1 -2.838920 4.526639 3.905136 97 1 -4.492215 3.787138 -3.217657 98 1 -4.883418 4.937127 -0.998531 99 8 -2.431141 0.103048 4.076442 100 6 0.643335 2.825717 -1.560247 101 6 1.325547 3.601454 -2.520111 102 8 1.963015 4.677353 -1.938480 103 6 1.622516 1.924124 1.919895 104 6 1.556697 2.403276 3.244899 105 8 1.059380 3.691474 3.298836 106 6 3.431091 1.151397 4.012701 107 6 2.315113 1.920911 4.319058 108 6 1.312741 5.436889 1.614619 109 6 1.747965 5.665761 0.310630 110 6 1.169152 3.479892 -3.903830 111 6 0.060037 2.776450 -4.355693 112 1 4.183307 0.927060 4.761159 113 1 2.170165 2.325702 5.314879 114 1 1.330690 6.221276 2.363347 115 1 2.102047 6.639713 -0.008608 116 1 1.803868 4.035289 -4.585435 117 1 -0.213054 2.772534 -5.405408 -------------------------------------------------------

Table S16. The optimized Cartesian coordinates of the oxa[28]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 1.704266 -2.970616 -1.247803 2 6 2.014248 -3.276184 0.140703 3 6 1.805261 2.762435 -1.453562 4 6 1.703659 2.970860 1.247876 5 6 -1.755284 3.195327 0.718838 6 6 -1.754691 -3.195540 -0.718959 7 6 -1.572102 -2.370066 1.870704 8 6 -1.965909 -1.008026 2.304536 9 6 -1.777087 3.223897 -0.737378 10 6 3.609315 0.053580 0.710609 11 6 2.781812 -0.320807 1.856172 12 6 1.955732 -1.470373 2.146083 13 6 2.825758 -4.426924 0.081515 14 6 2.662668 -3.709544 -1.980948 15 6 -2.650650 -4.223354 -1.096168 16 6 1.831427 -1.797724 3.515217 17 6 3.471646 0.218029 2.966203 18 6 4.837596 0.441707 1.272150 19 8 4.698599 0.728628 2.609799 20 6 1.857813 3.721438 -2.480987 21 6 2.661986 3.709864 1.981082

24

22 6 -2.651484 4.222976 1.095903 23 6 -2.316281 4.490578 -1.050077 24 8 -2.946859 5.044729 0.036220 25 6 -1.703158 -1.006363 3.695515 26 8 -1.180683 -2.198759 4.131986 27 6 -1.322618 -3.058090 3.073964 28 8 3.329641 -4.607977 -1.183386 29 6 -0.915367 -2.716551 -1.783026 30 6 -1.428468 -2.923896 -3.079796 31 6 3.609094 -0.052588 -0.711151 32 6 4.837157 -0.440898 -1.273073 33 6 1.806057 -2.761714 1.453582 34 6 1.858659 -3.720589 2.481122 35 8 1.649871 -3.147938 3.712337 36 6 3.470641 -0.217278 -2.966674 37 8 4.697670 -0.727937 -2.610629 38 6 2.781181 0.321704 -1.856465 39 6 -1.703915 1.005451 -3.695282 40 6 -1.966434 1.007226 -2.304258 41 6 -3.839770 -0.110714 -0.704737 42 6 6.076977 0.281921 0.635845 43 6 6.076759 -0.281184 -0.637168 44 6 2.258875 -1.013451 4.592333 45 6 3.142154 0.015692 4.308096 46 6 3.000164 -5.327339 1.135478 47 6 2.404599 -5.004141 2.350742 48 1 6.998153 0.506732 1.161910 49 1 6.997756 -0.506058 -1.163519 50 1 2.078796 -1.343705 5.609419 51 1 3.681613 0.535950 5.091325 52 1 3.559450 -6.245484 0.994663 53 1 2.481147 -5.653302 3.215982 54 6 0.544829 2.559826 1.997061 55 6 0.698451 2.604398 3.399682 56 6 1.954975 1.471199 -2.146228 57 6 1.830531 1.798683 -3.515312 58 8 1.649002 3.148922 -3.712263 59 6 2.257741 1.014445 -4.592548 60 6 3.140945 -0.014809 -4.308508 61 1 2.077521 1.344773 -5.609584 62 1 3.680181 -0.535098 -5.091872 63 6 -0.915940 2.716571 1.782974 64 6 -1.429114 2.923972 3.079701 65 8 -0.508956 2.633096 4.054916 66 6 2.013564 3.276664 -0.140604 67 6 2.824921 4.427502 -0.081298 68 8 3.328829 4.608462 1.183598 69 6 -3.132781 4.439382 2.385952 70 6 -2.549570 3.698666 3.403735 71 6 1.834430 3.037898 4.094475 72 6 2.827723 3.672714 3.364552 73 6 2.999094 5.328130 -1.135120 74 6 2.403580 5.005038 -2.350428 75 1 -3.886859 5.194023 2.579277 76 1 -2.822222 3.840657 4.443368 77 1 1.823769 3.056690 5.178705 78 1 3.643577 4.204407 3.841222 79 1 3.558172 6.246378 -0.994145 80 1 2.480009 5.654383 -3.215543 81 6 -3.839614 0.109806 0.705370 82 6 -5.084621 0.511372 1.233860 83 6 -1.572663 2.369382 -1.870663 84 6 -1.323445 3.057261 -3.074063

25

85 6 -2.168949 5.138431 -2.278613 86 6 -1.553693 4.421791 -3.295924 87 1 -2.519220 6.155266 -2.416348 88 1 -1.394768 4.841561 -4.282776 89 8 -1.181570 2.197801 -4.131985 90 6 -1.776458 -3.224362 0.737261 91 6 -2.315474 -4.491150 1.049792 92 8 -2.945937 -5.045265 -0.036586 93 6 0.545424 -2.559724 -1.997055 94 6 0.699083 -2.604263 -3.399673 95 8 -0.508302 -2.632804 -4.054948 96 6 2.828404 -3.672479 -3.364418 97 6 1.835065 -3.037828 -4.094413 98 6 -2.548641 -3.698934 -3.403959 99 6 -3.131739 -4.439862 -2.386276 100 6 -2.168092 -5.139166 2.278239 101 6 -1.552810 -4.422660 3.295638 102 1 3.644330 -4.204111 -3.841033 103 1 1.824416 -3.056781 -5.178641 104 1 -2.821115 -3.841035 -4.443627 105 1 -3.885578 -5.194709 -2.579715 106 1 -2.518315 -6.156035 2.415837 107 1 -1.393856 -4.842609 4.282411 108 6 -2.980267 -0.070870 1.876654 109 6 -3.707138 0.545850 2.925077 110 8 -4.963658 0.924642 2.533754 111 6 -2.980616 0.069927 -1.876161 112 6 -3.707713 -0.546775 -2.924442 113 8 -4.964217 -0.925415 -2.532904 114 6 -2.251413 0.148733 -4.654142 115 6 -3.329601 -0.622796 -4.263096 116 6 -6.325120 -0.314056 -0.618828 117 6 -6.324959 0.313474 0.619933 118 6 -3.328871 0.621739 4.263686 119 6 -2.250637 -0.149806 4.654539 120 1 -1.963317 0.249895 -5.694411 121 1 -3.931897 -1.178126 -4.973016 122 1 -7.241548 -0.572841 -1.137273 123 1 -7.241258 0.572373 1.138552 124 1 -3.931140 1.176950 4.973721 125 1 -1.962429 -0.251076 5.694768 126 6 -5.084911 -0.512136 -1.232984 -------------------------------------------------------

Table S17. The optimized Cartesian coordinates of the oxa[30]circulene in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 2.887537 -1.752598 1.662249 2 6 -0.097777 2.838221 -4.569310 3 6 -1.640067 1.946002 -2.283349 4 6 -0.497427 2.825561 -2.076432 5 6 -0.304176 5.393163 0.682445 6 6 -0.077600 4.035802 0.360003 7 6 0.074026 3.376979 1.662249 8 6 -0.459065 4.324531 2.575403 9 8 -0.683006 5.539413 1.988544 10 6 0.905489 2.358458 2.278541 11 6 0.731292 2.233919 3.678358 12 6 -0.060561 3.032556 4.509297

26

13 6 -0.620575 4.162396 3.948380 14 1 -1.095542 4.936272 4.540496 15 1 -0.058184 2.853525 5.578420 16 6 2.276571 1.809842 2.046012 17 6 2.750872 1.515921 3.342850 18 8 1.758168 1.556396 4.281727 19 6 3.323509 1.944256 1.064456 20 6 4.591407 2.289661 1.596453 21 6 5.026513 2.049188 2.896169 22 6 4.079170 1.564250 3.780219 23 1 4.300614 1.391603 4.826753 24 1 6.042082 2.281932 3.195740 25 6 3.482552 2.148267 -0.369505 26 6 4.631274 2.966886 -0.477955 27 8 5.358945 2.960558 0.681754 28 6 2.949908 1.703248 -1.624200 29 6 3.217970 2.586951 -2.691410 30 6 4.154033 3.627206 -2.697219 31 6 4.962828 3.755040 -1.579363 32 1 5.806539 4.434858 -1.542159 33 1 4.318199 4.199398 -3.603200 34 6 2.505320 0.447339 -2.283349 35 6 2.354752 0.828899 -3.640555 36 8 2.696814 2.133567 -3.868038 37 6 2.695721 -0.981997 -2.076432 38 6 2.836244 -1.730344 -3.274872 39 6 2.506860 -1.334433 -4.569310 40 6 2.219823 -0.000480 -4.755194 41 1 2.083548 0.434791 -5.738498 42 1 2.592116 -2.037786 -5.388995 43 6 3.279722 -1.874503 -1.051681 44 6 3.964805 -2.859266 -1.796193 45 8 3.554850 -2.879572 -3.099264 46 6 0.000000 6.485090 -0.134059 47 6 0.525133 6.199806 -1.384638 48 6 0.493795 4.863255 -1.796193 49 6 -0.016494 3.777574 -1.051681 50 1 0.849238 6.973211 -2.071823 51 1 -0.112984 7.497812 0.236089 52 6 0.080400 3.321432 -3.274872 53 8 0.716357 4.518376 -3.099264 54 6 -1.109496 1.922663 -4.755194 55 6 -1.895224 1.624825 -3.640555 56 1 0.468717 3.263731 -5.388995 57 1 -1.418314 1.587010 -5.738498 58 6 -2.950010 1.703071 -1.624200 59 6 -3.849350 1.493368 -2.691410 60 8 -3.196130 1.268726 -3.868038 61 6 -3.601730 1.941845 -0.369505 62 6 -4.885036 2.527358 -0.477955 63 6 -5.733373 2.420415 -1.579363 64 6 -5.218269 1.783896 -2.697219 65 8 -5.243391 3.160703 0.681754 66 6 -4.278608 2.831445 1.596453 67 6 -3.345529 1.906115 1.064456 68 6 -4.287906 3.328494 2.896169 69 6 -3.394265 2.750540 3.780219 70 6 -2.688262 1.624365 3.342850 71 6 -2.705655 1.066648 2.046012 72 1 -4.997252 4.091630 3.195740 73 1 -3.355470 3.028639 4.826753 74 1 -6.743969 2.811181 -1.542159 75 1 -5.795884 1.639971 -3.603200

27

76 6 -2.495229 -0.395053 2.278541 77 6 -2.300277 -0.483642 3.678358 78 8 -2.226962 0.744420 4.281727 79 6 -2.961563 -1.624381 1.662249 80 6 -3.515622 -2.559828 2.575403 81 6 -3.294453 -2.618632 3.948380 82 6 -2.595990 -1.568726 4.509297 83 1 -2.442133 -1.477151 5.578420 84 1 -3.727166 -3.416903 4.540496 85 6 -3.456307 -2.085104 0.360003 86 6 -4.518528 -2.960005 0.682445 87 8 -4.455770 -3.361207 1.988544 88 6 -3.263228 -1.903071 -1.051681 89 6 -4.458600 -2.003988 -1.796193 90 6 -5.631756 -2.645125 -1.384638 91 6 -5.616253 -3.242545 -0.134059 92 1 -6.436804 -3.846753 0.236089 93 1 -6.463597 -2.751144 -2.071823 94 6 -2.198295 -1.843565 -2.076432 95 6 -2.916644 -1.591088 -3.274872 96 8 -4.271207 -1.638805 -3.099264 97 6 -0.865253 -2.393340 -2.283349 98 6 -0.459528 -2.453725 -3.640555 99 6 -1.110327 -1.922183 -4.755194 100 6 -2.409083 -1.503788 -4.569310 101 1 -3.060832 -1.225945 -5.388995 102 1 -0.665234 -2.021801 -5.738498 103 6 0.000102 -3.406319 -1.624200 104 6 0.631380 -4.080319 -2.691410 105 8 0.499316 -3.402293 -3.868038 106 6 1.064236 -5.411101 -2.697219 107 6 0.770546 -6.175455 -1.579363 108 6 0.253761 -5.494244 -0.477955 109 6 0.119178 -4.090112 -0.369505 110 1 0.937430 -7.246039 -1.542159 111 1 1.477686 -5.839369 -3.603200 112 6 0.022020 -3.850371 1.064456 113 6 -0.312799 -5.121106 1.596453 114 8 -0.115554 -6.121261 0.681754 115 6 -0.062610 -3.140286 3.342850 116 6 0.429084 -2.876490 2.046012 117 8 0.468795 -2.300816 4.281727 118 6 1.568985 -1.750277 3.678358 119 6 1.589740 -1.963406 2.278541 120 6 2.656551 -1.463830 4.509297 121 6 3.915028 -1.543764 3.948380 122 6 3.974686 -1.764704 2.575403 123 1 4.822707 -1.519369 4.540496 124 1 2.500317 -1.376373 5.578420 125 6 3.533907 -1.950698 0.360003 126 6 4.822704 -2.433157 0.682445 127 8 5.138776 -2.178206 1.988544 128 6 5.106623 -3.554681 -1.384638 129 6 5.616253 -3.242545 -0.134059 130 1 5.614359 -4.222067 -2.071823 131 1 6.549788 -3.651059 0.236089 132 6 -0.684905 -4.314790 3.780219 133 6 -0.738608 -5.377682 2.896169 134 1 -0.945144 -4.420242 4.826753 135 1 -1.044829 -6.373563 3.195740 -------------------------------------------------------

28

Table S18. The optimized Cartesian coordinates of the [4]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 -0.635285 0.825530 1.363271 2 6 0.780177 0.690208 1.363269 3 6 -0.780177 -0.690208 1.363269 4 6 0.635285 -0.825530 1.363271 5 6 1.521239 1.085772 0.274714 6 6 -1.287996 1.354362 0.274736 7 6 -0.497853 2.177294 -0.594171 8 6 0.901358 2.043512 -0.594187 9 6 2.201519 -0.210482 -0.286245 10 6 1.287996 -1.354362 0.274736 11 6 -1.521239 -1.085772 0.274714 12 6 -0.901358 -2.043512 -0.594187 13 6 0.497853 -2.177294 -0.594171 14 6 -2.201519 0.210482 -0.286245 15 1 -0.958182 2.707781 -1.424376 16 1 1.453837 2.477152 -1.424415 17 1 -1.453837 -2.477152 -1.424415 18 1 0.958182 -2.707781 -1.424376 19 8 3.037645 -0.290389 -1.148212 20 8 -3.037645 0.290389 -1.148212 --------------------------------------------------------

Table S19. The optimized Cartesian coordinates of the [6]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 0.098074 1.407316 -0.804786 2 6 -1.149779 0.817380 -0.804792 3 6 1.282762 0.587048 -0.804792 4 6 1.169735 -0.788593 -0.804786 5 6 -0.132983 -1.404428 -0.804792 6 6 -1.267809 -0.618724 -0.804786 7 6 0.332310 2.630446 -0.163113 8 6 -2.243636 1.412698 -0.163176 9 6 2.345251 1.236697 -0.163176 10 6 2.111878 -1.603012 -0.163113 11 6 -0.101614 -2.649395 -0.163176 12 6 -2.444188 -1.027434 -0.163113 13 6 -1.297823 -3.131312 0.375914 14 6 -2.474342 -2.316706 0.376036 15 6 -2.062885 2.689604 0.375914 16 6 -0.769155 3.301196 0.376036 17 6 3.243497 -0.984491 0.376036 18 6 3.360707 0.441709 0.375914 19 6 1.841635 2.659776 0.167746 20 6 -3.224252 0.265015 0.167746 21 6 1.382616 -2.924791 0.167746 22 1 -1.314833 -4.070368 0.922337 23 1 -3.347233 -2.662996 0.922682 24 1 -2.867626 3.173862 0.922337 25 1 -0.632606 4.230287 0.922682 26 1 3.979839 -1.567290 0.922682 27 1 4.182458 0.896505 0.922337

29

28 8 2.461861 3.555447 0.694060 29 8 1.848177 -3.909758 0.694060 30 8 -4.310038 0.354310 0.694060 --------------------------------------------------------

Table S20. The optimized Cartesian coordinates of the [8]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 -1.182375 -3.089871 0.000000 2 6 -0.748224 -1.734205 0.000000 3 6 -1.734205 -0.748224 0.000000 4 6 -1.734205 0.748224 0.000000 5 6 -3.089871 1.182375 0.000000 6 6 -3.089871 -1.182375 0.000000 7 6 -0.748224 1.734205 0.000000 8 6 -3.993150 0.000000 0.000000 9 6 -1.182375 3.089871 0.000000 10 6 -3.495323 -2.506201 0.000000 11 6 -2.506201 -3.495323 0.000000 12 6 -2.506201 3.495323 0.000000 13 6 -3.495323 2.506201 0.000000 14 1 -4.554948 -2.742680 0.000000 15 1 -2.742680 -4.554948 0.000000 16 1 -2.742680 4.554948 0.000000 17 1 -4.554948 2.742680 0.000000 18 6 0.748224 -1.734205 0.000000 19 6 1.182375 -3.089871 0.000000 20 6 1.734205 -0.748224 0.000000 21 6 1.734205 0.748224 0.000000 22 6 0.748224 1.734205 0.000000 23 6 3.089871 -1.182375 0.000000 24 6 3.089871 1.182375 0.000000 25 6 1.182375 3.089871 0.000000 26 6 3.495323 -2.506201 0.000000 27 6 2.506201 -3.495323 0.000000 28 6 2.506201 3.495323 0.000000 29 6 3.495323 2.506201 0.000000 30 1 4.554948 -2.742680 0.000000 31 1 2.742680 -4.554948 0.000000 32 1 2.742680 4.554948 0.000000 33 1 4.554948 2.742680 0.000000 34 6 3.993150 0.000000 0.000000 35 6 0.000000 -3.993150 0.000000 36 6 0.000000 3.993150 0.000000 37 8 0.000000 5.212010 0.000000 38 8 5.212010 0.000000 0.000000 39 8 0.000000 -5.212010 0.000000 40 8 -5.212010 0.000000 0.000000 --------------------------------------------------------

Table S21. The optimized Cartesian coordinates of the [10]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory--------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z --------------------------------------------------------- 1 6 -0.755184 -4.547133 -0.623731

30

2 6 1.490137 2.660502 -1.875179 3 6 1.603196 4.010629 -1.598742 4 6 0.745048 4.538724 -0.630401 5 6 -0.023823 3.646790 0.088431 6 6 0.037233 2.219016 -0.009198 7 6 0.683969 1.721345 -1.154820 8 6 0.409389 0.569927 -2.087383 9 6 -0.396106 -0.583255 -2.089350 10 6 -0.680938 -1.731394 -1.156020 11 6 -0.043017 -2.228266 -0.004982 12 6 0.666859 -1.701203 1.215145 13 6 0.428048 -0.620208 2.083210 14 6 -0.436806 0.614376 2.080825 15 6 -0.675743 1.692604 1.209437 16 6 -1.110067 4.030982 1.023150 17 6 -1.443313 2.779463 1.743907 18 6 -2.054491 2.804605 2.983762 19 6 -1.725662 1.786398 3.880973 20 6 -0.869471 0.799178 3.435561 21 6 -0.005077 0.001085 4.338010 22 6 0.858952 -0.801167 3.438915 23 6 1.712323 -1.788784 3.888709 24 6 2.039134 -2.811263 2.995550 25 6 1.430001 -2.788643 1.754548 26 1 -2.615818 3.684637 3.282971 27 1 -2.002788 1.821618 4.930194 28 1 1.988317 -1.820852 4.938311 29 1 2.597400 -3.691878 3.298742 30 6 1.094716 -4.041009 1.036147 31 6 0.012767 -3.655873 0.096724 32 6 -1.605016 -4.018782 -1.599273 33 6 -1.485053 -2.669918 -1.879479 34 6 -1.828522 -2.126718 -3.215729 35 6 -0.919862 -0.963188 -3.365950 36 6 -0.508612 -0.470959 -4.588769 37 6 0.541454 0.452339 -4.585621 38 6 0.943033 0.947285 -3.360616 39 6 1.847509 2.113408 -3.206169 40 1 2.232249 4.633216 -2.227594 41 1 0.634032 5.604975 -0.459309 42 1 0.997574 0.832585 -5.494345 43 1 -0.958247 -0.852692 -5.500083 44 1 -2.232037 -4.641143 -2.230406 45 1 -0.648995 -5.613231 -0.448761 46 8 -1.570385 5.145939 1.195037 47 8 2.619394 2.570391 -4.029693 48 8 -2.593422 -2.584741 -4.045173 49 8 1.549809 -5.157290 1.213342 50 8 -0.004691 0.004231 5.556873 -------------------------------------------------------

Table S22. The optimized Cartesian coordinates of the [12]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.370770 1.290247 1.246301 2 6 -2.239668 0.367350 0.648700 3 6 0.374361 -2.200919 0.591738 4 6 1.370772 -1.290248 1.246299 5 6 2.239669 -0.367351 0.648700

31

6 6 -0.374361 2.200919 0.591739 7 6 0.374753 2.200970 -0.591451 8 6 1.370840 1.290182 -1.246342 9 6 2.239620 0.366994 -0.649022 10 6 -0.374752 -2.200970 -0.591453 11 6 -1.370839 -1.290181 -1.246343 12 6 -2.239619 -0.366994 -0.649022 13 6 -3.577494 0.338634 1.140601 14 6 -3.968302 0.877240 2.354980 15 6 -3.034299 1.649305 3.058511 16 6 -1.820407 1.921974 2.441719 17 6 -1.147774 3.248016 2.583481 18 6 -0.491552 3.455843 1.254618 19 6 -3.577337 -0.337978 -1.141205 20 6 -4.484031 0.000468 -0.000406 21 6 -1.820432 -1.922016 -2.441720 22 6 -3.034122 -1.649101 -3.058802 23 6 -3.968040 -0.876637 -2.355594 24 6 -0.492230 -3.456021 -1.254041 25 6 -1.148200 -3.248310 -2.583048 26 6 -0.197634 -4.678100 -0.672827 27 6 0.196626 -4.677986 0.673705 28 6 0.491550 -3.455843 1.254618 29 6 1.147775 -3.248018 2.583480 30 6 1.820407 -1.921975 2.441718 31 6 3.034298 -1.649306 3.058511 32 6 3.968302 -0.877241 2.354980 33 6 3.577495 -0.338635 1.140601 34 6 3.577338 0.337977 -1.141206 35 6 4.484032 -0.000472 -0.000407 36 6 3.968040 0.876638 -2.355594 37 6 1.820433 1.922017 -2.441719 38 6 3.034123 1.649102 -3.058802 39 6 1.148202 3.248312 -2.583046 40 6 0.492229 3.456022 -1.254040 41 6 -0.196631 4.677987 0.673704 42 6 0.197630 4.678100 -0.672828 43 1 -5.004304 0.804453 2.671833 44 1 -3.306864 2.188840 3.960847 45 1 -3.306677 -2.188724 -3.961089 46 1 -5.003957 -0.803611 -2.672670 47 1 -0.340965 -5.594388 -1.237140 48 1 0.339753 -5.594174 1.238231 49 1 3.306864 -2.188841 3.960847 50 1 5.004304 -0.804454 2.671833 51 1 5.003957 0.803611 -2.672671 52 1 3.306677 2.188724 -3.961089 53 1 -0.339759 5.594175 1.238230 54 1 0.340960 5.594388 -1.237140 55 8 -1.210972 -4.038854 -3.504365 56 8 1.210441 -4.038353 3.504983 57 8 -5.700735 0.000652 -0.000539 58 8 -1.210440 4.038352 3.504984 59 8 1.210970 4.038854 -3.504365 60 8 5.700737 -0.000649 -0.000539 ----------------------------------------------------------

32

Table S23. The optimized Cartesian coordinates of the [14]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 1.814911 1.381394 0.454722 2 6 0.856590 2.285524 -0.013870 3 6 0.571082 -0.402218 -2.316850 4 6 1.189106 -1.386274 -1.383654 5 6 0.559590 -2.232603 -0.459820 6 6 1.756149 0.258457 1.446994 7 6 0.734999 -0.095185 2.334804 8 6 -0.734999 0.095185 2.334804 9 6 -0.856590 -2.285524 -0.013870 10 6 -0.571082 0.402218 -2.316850 11 6 -1.189106 1.386274 -1.383654 12 6 -0.559590 2.232603 -0.459820 13 6 1.246747 3.654140 -0.056123 14 6 3.172629 1.799450 0.385796 15 6 4.046059 0.757255 1.016584 16 6 3.087867 -0.052842 1.833274 17 6 -1.120238 3.530029 -0.279846 18 6 0.000000 4.488740 -0.012028 19 6 -2.410046 1.836108 -1.960931 20 6 -1.235178 0.557245 -3.566420 21 6 -2.551744 1.234313 -3.325573 22 6 1.235178 -0.557245 -3.566420 23 6 2.551744 -1.234313 -3.325573 24 6 2.410046 -1.836108 -1.960931 25 6 1.120238 -3.530029 -0.279846 26 6 -1.246747 -3.654140 -0.056123 27 6 0.000000 -4.488740 -0.012028 28 6 -1.121578 0.410605 3.668029 29 6 0.000000 0.000000 4.576895 30 6 1.121578 -0.410605 3.668029 31 6 -1.814911 -1.381394 0.454722 32 6 -3.172629 -1.799450 0.385796 33 6 -1.756149 -0.258457 1.446994 34 6 -3.087867 0.052842 1.833274 35 6 -4.046059 -0.757255 1.016584 36 6 -2.565304 -4.075578 -0.031330 37 6 -3.566162 -3.095795 0.086910 38 6 -3.421437 0.629073 3.052736 39 6 -2.418021 0.741178 4.028175 40 6 2.418021 -0.741178 4.028175 41 6 3.421437 -0.629073 3.052736 42 6 2.565304 4.075578 -0.031330 43 6 3.566162 3.095795 0.086910 44 6 -3.065011 2.995644 -1.568281 45 6 -2.384902 3.885981 -0.722992 46 6 0.663582 -0.233584 -4.785550 47 6 -0.663582 0.233584 -4.785550 48 6 2.384902 -3.885981 -0.722992 49 6 3.065011 -2.995644 -1.568281 50 1 -2.800501 -5.134043 -0.086122 51 1 -4.621854 -3.349678 0.081164 52 1 -4.465318 0.815498 3.287366 53 1 -2.651345 0.985120 5.060163 54 1 2.651345 -0.985120 5.060163 55 1 4.465318 -0.815498 3.287366 56 1 2.800501 5.134043 -0.086122 57 1 4.621854 3.349678 0.081164

33

58 1 -3.991612 3.279326 -2.058657 59 1 -2.756372 4.890925 -0.545474 60 1 1.215112 -0.402217 -5.705393 61 1 -1.215112 0.402217 -5.705393 62 1 2.756372 -4.890925 -0.545474 63 1 3.991612 -3.279326 -2.058657 64 8 0.067480 -5.692266 0.148010 65 8 -5.257824 -0.678309 0.977566 66 8 0.000000 0.000000 5.792890 67 8 5.257824 0.678309 0.977566 68 8 -0.067480 5.692266 0.148010 69 8 -3.471670 1.352430 -4.111054 70 8 3.471670 -1.352430 -4.111054 -------------------------------------------------------

Table S24. The optimized Cartesian coordinates of the [16]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 2.231535 0.629902 1.065268 2 6 2.561316 0.508132 -0.291157 3 6 -1.044723 -1.084800 1.866829 4 6 -2.231535 -0.629902 1.065268 5 6 -2.561316 -0.508132 -0.291157 6 6 -0.048165 1.915967 1.557861 7 6 -0.508064 2.561208 0.291171 8 6 -0.629795 2.231426 -1.065266 9 6 -1.916078 -0.048170 -1.557848 10 6 0.508064 -2.561208 0.291171 11 6 0.629795 -2.231426 -1.065266 12 6 1.084852 -1.044669 -1.866817 13 6 3.896685 0.885516 -0.635476 14 6 3.332493 0.559626 1.972924 15 6 0.979061 -1.401486 -3.246367 16 6 0.559434 -3.332374 -1.972913 17 6 0.885565 -3.896548 0.635461 18 6 -1.401498 -0.979004 3.246382 19 6 -2.811661 -0.518552 3.369151 20 6 -3.332493 -0.559626 1.972924 21 6 -3.896685 -0.885516 -0.635476 22 6 -2.665713 -0.610960 -2.637494 23 6 -3.934941 -1.180959 -2.098134 24 6 -0.559434 3.332374 -1.972913 25 6 -0.885565 3.896548 0.635461 26 6 0.518227 -2.811522 -3.369116 27 6 -1.181051 3.934757 2.098125 28 6 -0.979061 1.401486 -3.246367 29 6 -0.518227 2.811522 -3.369116 30 6 -1.084852 1.044669 -1.866817 31 6 1.044723 1.084800 1.866829 32 6 2.811661 0.518552 3.369151 33 6 1.401498 0.979004 3.246382 34 6 0.048165 -1.915967 1.557861 35 6 0.611085 -2.665506 2.637481 36 6 1.181051 -3.934757 2.098125 37 6 1.916078 0.048170 -1.557848 38 6 2.665713 0.610960 -2.637494 39 6 3.934941 1.180959 -2.098134 40 6 0.327867 -2.453380 3.974975

34

41 6 -0.702393 -1.558798 4.290323 42 6 -4.661558 -0.682102 1.609613 43 6 -2.453764 -0.327577 -3.974979 44 6 -1.559099 0.702610 -4.290320 45 6 -0.979061 4.939830 -0.265881 46 6 0.702393 1.558798 4.290323 47 6 -0.327867 2.453380 3.974975 48 6 4.939972 0.978984 0.265846 49 6 1.559099 -0.702610 -4.290320 50 6 2.453764 0.327577 -3.974979 51 6 0.682020 -4.661438 -1.609608 52 6 0.979061 -4.939830 -0.265881 53 1 0.806657 -3.069423 4.730019 54 1 -1.056870 -1.426596 5.308213 55 1 -3.069943 -0.806252 -4.729985 56 1 -1.426927 1.057157 -5.308188 57 1 -1.250058 5.933061 0.078348 58 1 1.056870 1.426596 5.308213 59 1 -0.806657 3.069423 4.730019 60 1 1.426927 -1.057157 -5.308188 61 1 3.069943 0.806252 -4.729985 62 1 0.640818 -5.434452 -2.370654 63 1 1.250058 -5.933061 0.078348 64 6 4.661558 0.682102 1.609613 65 6 -0.682020 4.661438 -1.609608 66 1 -0.640818 5.434452 -2.370654 67 6 -4.939972 -0.978984 0.265846 68 1 -5.434581 -0.640977 2.370654 69 1 -5.933216 -1.249902 -0.078407 70 1 5.933216 1.249902 -0.078407 71 1 5.434581 0.640977 2.370654 72 6 -0.611085 2.665506 2.637481 73 8 0.262026 -3.433003 -4.383848 74 8 1.711092 -4.838766 2.716428 75 8 -3.433004 -0.261817 4.383828 76 8 -4.838903 -1.711098 -2.716433 77 8 -0.262026 3.433003 -4.383848 78 8 -1.711092 4.838766 2.716428 79 8 3.433004 0.261817 4.383828 80 8 4.838903 1.711098 -2.716433 -------------------------------------------------------

Table S25. The optimized Cartesian coordinates of the [18]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 -0.017939 0.758070 2.686482 2 6 0.017939 -0.758070 2.686482 3 6 -0.393698 1.872855 -1.852841 4 6 -0.021477 0.706112 -2.757187 5 6 0.021477 -0.706112 -2.757187 6 6 1.432411 2.102419 0.756167 7 6 2.440648 1.389200 0.062530 8 6 2.933732 -0.039369 0.015502 9 6 0.393698 -1.872855 -1.852841 10 6 -2.933732 0.039369 0.015502 11 6 -2.440648 -1.389200 0.062530 12 6 -1.432411 -2.102419 0.756167 13 6 0.375067 -1.116494 4.034721 14 6 -0.375067 1.116494 4.034721

35

15 6 1.511636 3.528996 0.624073 16 6 -1.511636 -3.528996 0.624073 17 6 -3.512381 -2.180719 -0.478984 18 6 -4.368677 -0.054049 0.029086 19 6 -4.756487 -1.379015 -0.502954 20 6 0.118280 3.047614 -2.511313 21 6 0.624575 2.711352 -3.857055 22 6 0.284727 1.287458 -4.037181 23 6 -0.284727 -1.287458 -4.037181 24 6 -0.118280 -3.047614 -2.511313 25 6 -0.624575 -2.711352 -3.857055 26 6 4.368677 0.054049 0.029086 27 6 4.756487 1.379015 -0.502954 28 6 3.512381 2.180719 -0.478984 29 6 0.000000 0.000000 4.932373 30 6 3.343247 -2.347689 0.423538 31 6 0.411070 1.836843 1.879601 32 6 0.000000 3.127046 2.358811 33 6 0.567787 4.206163 1.532444 34 6 -2.440797 1.355809 -0.090061 35 6 -3.343247 2.347689 0.423538 36 6 -0.411070 -1.836843 1.879601 37 6 0.000000 -3.127046 2.358811 38 6 -0.567787 -4.206163 1.532444 39 6 -1.537312 3.502417 -0.486807 40 6 -2.705684 3.674801 0.400300 41 6 -1.322337 2.116388 -0.804967 42 6 1.537312 -3.502417 -0.486807 43 6 2.705684 -3.674801 0.400300 44 6 1.322337 -2.116388 -0.804967 45 6 2.440797 -1.355809 -0.090061 46 6 -0.941702 4.597889 -1.075323 47 6 -0.087704 4.360227 -2.148176 48 6 0.224037 0.661419 -5.263956 49 6 -0.224037 -0.661419 -5.263956 50 6 -5.247498 0.948227 0.377027 51 6 -4.682000 2.178462 0.718068 52 6 -2.455729 -4.251387 -0.078981 53 6 -3.527549 -3.551846 -0.623810 54 6 0.738577 -2.370481 4.475458 55 6 0.635024 -3.410794 3.553658 56 6 -0.635024 3.410794 3.553658 57 6 -0.738577 2.370481 4.475458 58 6 3.527549 3.551846 -0.623810 59 6 2.455729 4.251387 -0.078981 60 6 4.682000 -2.178462 0.718068 61 6 5.247498 -0.948227 0.377027 62 6 0.087704 -4.360227 -2.148176 63 6 0.941702 -4.597889 -1.075323 64 1 -1.208674 5.591848 -0.732389 65 1 0.343614 5.152346 -2.752287 66 1 0.458939 1.218187 -6.165365 67 1 -0.458939 -1.218187 -6.165365 68 1 -6.316247 0.759521 0.372332 69 1 -5.258276 3.022620 1.083058 70 1 -2.393004 -5.335150 -0.080424 71 1 -4.400005 -4.037381 -1.049652 72 1 1.011671 -2.521000 5.515156 73 1 0.889948 -4.440494 3.782954 74 1 -0.889948 4.440494 3.782954 75 1 -1.011671 2.521000 5.515156 76 1 4.400005 4.037381 -1.049652 77 1 2.393004 5.335150 -0.080424

36

78 1 5.258276 -3.022620 1.083058 79 1 6.316247 -0.759521 0.372332 80 1 -0.343614 -5.152346 -2.752287 81 1 1.208674 -5.591848 -0.732389 82 8 0.000000 0.000000 6.150945 83 8 0.383403 5.406862 1.649455 84 8 5.871523 1.738160 -0.838569 85 8 3.104604 -4.702540 0.920278 86 8 -0.383403 -5.406862 1.649455 87 8 -1.141200 -3.457220 -4.671354 88 8 1.141200 3.457220 -4.671354 89 8 -3.104604 4.702540 0.920278 90 8 -5.871523 -1.738160 -0.838569 -------------------------------------------------------

Table S26. The optimized Cartesian coordinates of the [20]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 1.424040 -0.759454 -3.824586 2 6 2.475215 0.215299 -4.124784 3 6 2.985141 0.145667 -0.495195 4 6 4.386786 0.499904 -0.593919 5 6 5.111745 -0.197072 0.480547 6 6 4.067027 -0.667257 1.406064 7 6 2.798568 -0.100425 1.004792 8 6 5.015132 1.113021 -1.650270 9 6 4.258209 1.241291 -2.807275 10 6 3.059674 0.556196 -2.834053 11 6 2.360690 -0.086091 -1.745983 12 1 4.624902 1.696539 -3.723302 13 1 6.068569 1.372476 -1.586379 14 6 4.386786 -1.217026 2.625856 15 6 3.459749 -1.021688 3.636204 16 6 2.390292 -0.196322 3.352569 17 6 1.972525 0.332607 2.078177 18 1 5.371227 -1.648262 2.787163 19 1 3.614542 -1.344503 4.662437 20 6 1.250421 -0.972980 -2.409302 21 6 1.653965 0.401334 4.460750 22 6 0.745759 1.369493 3.844472 23 6 0.844821 1.375909 2.406487 24 6 -0.026251 2.160870 4.667897 25 6 -0.800382 3.135967 4.063689 26 6 -0.720367 3.215674 2.692948 27 6 0.017019 2.361607 1.790039 28 1 0.035111 2.013388 5.742454 29 1 -1.386499 3.869375 4.611421 30 6 -1.097863 4.480723 2.041489 31 6 -0.366369 4.453517 0.767084 32 6 -0.063583 3.078502 0.445063 33 6 -0.002576 5.575654 0.060937 34 6 0.754919 5.340911 -1.086737 35 6 0.754014 4.042574 -1.545599 36 6 0.139627 2.887804 -0.938932 37 1 -0.271547 6.564108 0.422402 38 1 1.246283 6.119873 -1.662860 39 6 1.241059 3.687540 -2.880837 40 6 0.437681 2.508512 -3.239072 41 6 -0.254920 1.955674 -2.099155

37

42 6 0.234433 2.252770 -4.576169 43 6 -0.765967 1.348689 -4.880894 44 6 -1.424040 0.759454 -3.824586 45 6 -1.250421 0.972980 -2.409302 46 1 0.826661 2.779539 -5.319062 47 1 -1.053848 1.078390 -5.893416 48 6 -2.360690 0.086091 -1.745983 49 6 -3.059674 -0.556196 -2.834053 50 6 -2.475215 -0.215299 -4.124784 51 6 -4.258209 -1.241291 -2.807275 52 6 -5.015132 -1.113021 -1.650270 53 6 -4.386786 -0.499904 -0.593919 54 6 -2.985141 -0.145667 -0.495195 55 1 -4.624902 -1.696539 -3.723302 56 1 -6.068569 -1.372476 -1.586379 57 6 -5.111745 0.197072 0.480547 58 6 -4.067027 0.667257 1.406064 59 6 -2.798568 0.100425 1.004792 60 6 -4.386786 1.217026 2.625856 61 6 -3.459749 1.021688 3.636204 62 6 -2.390292 0.196322 3.352569 63 6 -1.972525 -0.332607 2.078177 64 1 -5.371227 1.648262 2.787163 65 1 -3.614542 1.344503 4.662437 66 6 0.254920 -1.955674 -2.099155 67 6 -0.437681 -2.508512 -3.239072 68 6 -0.234433 -2.252770 -4.576169 69 6 0.765967 -1.348689 -4.880894 70 1 1.053848 -1.078390 -5.893416 71 1 -0.826661 -2.779539 -5.319062 72 6 -1.241059 -3.687540 -2.880837 73 6 -0.754014 -4.042574 -1.545599 74 6 -0.139627 -2.887804 -0.938932 75 6 -0.754919 -5.340911 -1.086737 76 6 0.002576 -5.575654 0.060937 77 6 0.366369 -4.453517 0.767084 78 6 0.063583 -3.078502 0.445063 79 6 1.097863 -4.480723 2.041489 80 6 0.720367 -3.215674 2.692948 81 6 -0.017019 -2.361607 1.790039 82 1 0.271547 -6.564108 0.422402 83 1 -1.246283 -6.119873 -1.662860 84 6 0.800382 -3.135967 4.063689 85 6 0.026251 -2.160870 4.667897 86 6 -0.745759 -1.369493 3.844472 87 6 -0.844821 -1.375909 2.406487 88 6 -1.653965 -0.401334 4.460750 89 1 -0.035111 -2.013388 5.742454 90 1 1.386499 -3.869375 4.611421 91 8 6.318086 -0.335949 0.586682 92 8 1.813953 0.197912 5.655786 93 8 2.827463 0.599090 -5.231040 94 8 -2.063562 -4.277392 -3.559808 95 8 1.799686 -5.377750 2.474046 96 8 -6.318086 0.335949 0.586682 97 8 -1.813953 -0.197912 5.655786 98 8 -1.799686 5.377750 2.474046 99 8 2.063562 4.277392 -3.559808 100 8 -2.827463 -0.599090 -5.231040 --------------------------------------------------------

38

Table S27. The optimized Cartesian coordinates of the [22]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 -1.069071 4.066665 -2.082551 2 6 -0.447449 4.554095 -0.953159 3 6 0.085250 3.624354 -0.079409 4 6 0.001520 2.187695 -0.098290 5 6 -0.846912 1.694649 -1.189740 6 6 -1.188773 2.696269 -2.168847 7 1 -1.406324 4.680495 -2.911569 8 1 -0.292459 5.607254 -0.743216 9 6 0.807551 4.152983 1.082599 10 6 1.136280 2.998162 1.908282 11 6 0.884401 1.763207 1.222918 12 6 -1.398206 0.376154 -1.887439 13 6 -1.399940 0.653220 -3.298424 14 6 -1.482291 2.103577 -3.487060 15 6 1.550378 3.205838 3.213350 16 6 1.629431 2.093265 4.036948 17 6 1.531863 0.875575 3.399541 18 6 1.407509 0.652203 1.982662 19 1 1.692349 4.226015 3.554204 20 1 1.771959 2.135828 5.111896 21 6 1.523015 -0.422272 4.134473 22 6 1.754069 -1.451976 3.101714 23 6 1.964307 -0.771378 1.861293 24 6 2.195382 -2.734500 3.395364 25 6 3.094588 -3.352664 2.518314 26 6 3.566294 -2.581629 1.468171 27 6 3.005119 -1.325197 1.098438 28 6 4.974044 -2.670835 0.948894 29 6 5.257870 -1.297690 0.420165 30 6 4.020969 -0.618308 0.302226 31 1 3.565750 -4.302076 2.754025 32 1 1.970967 -3.157577 4.370139 33 6 6.476322 -0.683086 0.171618 34 6 6.476141 0.683139 -0.174668 35 6 5.257490 1.297567 -0.422685 36 6 4.020732 0.618025 -0.304153 37 1 7.401236 -1.238316 0.294492 38 1 7.400921 1.238483 -0.298026 39 6 4.973305 2.670581 -0.951531 40 6 3.565223 2.581264 -1.469926 41 6 3.004352 1.324809 -1.099828 42 6 3.092894 3.352256 -2.519819 43 6 2.193279 2.733991 -3.396366 44 6 1.752170 1.451470 -3.102368 45 6 1.963026 0.770992 -1.861993 46 6 1.405848 -0.652509 -1.982977 47 6 1.529288 -0.876073 -3.399824 48 6 1.520556 0.421708 -4.134915 49 1 3.563927 4.301655 -2.755830 50 1 1.968306 3.156969 -4.371055 51 6 -2.016092 -0.888390 -1.650133 52 6 -1.914724 -1.868861 -2.688980 53 6 -1.601146 -1.603100 -4.008077 54 6 -1.495268 -0.252167 -4.338618 55 1 -1.470335 0.113031 -5.359602 56 1 -1.596422 -2.402212 -4.741987 57 6 -2.540122 -3.165767 -2.261166

39

58 6 -3.130106 -1.424093 -0.794778 59 6 -3.465329 -2.750479 -1.174358 60 6 0.883045 -1.763365 -1.222699 61 6 1.134303 -2.998434 -1.908059 62 6 1.547382 -3.206331 -3.213442 63 6 1.626041 -2.093892 -4.037203 64 1 1.767831 -2.136542 -5.112246 65 1 1.688860 -4.226590 -3.554256 66 6 0.806038 -4.153095 -1.081913 67 6 0.084635 -3.624179 0.080551 68 6 0.000959 -2.187535 0.098964 69 6 -0.846706 -1.694068 1.190738 70 6 -1.187738 -2.695128 2.170649 71 6 -1.068069 -4.065561 2.084865 72 6 -0.447431 -4.553513 0.955113 73 1 -0.292655 -5.606780 0.745547 74 1 -1.404575 -4.679047 2.914444 75 6 -1.480032 -2.101582 3.488774 76 6 -1.397501 -0.375184 1.887900 77 6 -1.397810 -0.651307 3.299146 78 6 -1.492298 0.254789 4.338769 79 6 -1.599290 1.605474 4.007421 80 6 -1.914356 1.870193 2.688506 81 6 -2.015993 0.888952 1.650353 82 1 -1.594206 2.405066 4.740811 83 1 -1.466217 -0.109683 5.359986 84 6 -2.540999 3.166390 2.260415 85 6 -3.466684 2.749857 1.174480 86 6 -3.130765 1.423540 0.795302 87 6 -4.716733 3.315615 0.947434 88 6 -5.763698 2.504826 0.465093 89 6 -5.466378 1.188326 0.155823 90 6 -4.139161 0.695839 0.192789 91 6 -4.138717 -0.697305 -0.191518 92 6 -5.465542 -1.190807 -0.154019 93 6 -5.762115 -2.507397 -0.463639 94 6 -4.714843 -3.317244 -0.946855 95 6 -6.382459 -0.001628 0.001279 96 1 -6.785944 2.868266 0.424671 97 1 -4.908774 4.327703 1.291838 98 1 -6.784099 -2.871522 -0.422762 99 1 -4.906319 -4.329321 -1.291608 100 8 5.740528 3.609578 -1.033247 101 8 5.741515 -3.609652 1.030386 102 8 -2.401935 -4.250039 -2.792047 103 8 1.451256 -0.560701 5.342650 104 8 1.060470 5.324304 1.315663 105 8 -1.733221 2.701901 -4.520061 106 8 1.448421 0.559989 -5.343086 107 8 1.058925 -5.324463 -1.314776 108 8 -7.597263 -0.002063 0.001384 109 8 -2.403460 4.251004 2.790780 110 8 -1.729802 -2.699236 4.522439 -------------------------------------------------------

40

Table S28. The optimized Cartesian coordinates of the [24]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory--------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 3.735070 -3.135275 0.303513 2 6 -0.102307 -2.836896 -1.456447 3 6 -0.513476 -3.416072 -0.249860 4 6 -0.546714 -3.036497 1.182278 5 6 -0.252563 -4.212734 1.933787 6 6 -0.493861 -5.389219 1.032076 7 6 -0.846491 -4.801647 -0.306452 8 6 3.774481 1.886941 1.937478 9 6 4.915071 2.265990 1.037030 10 6 4.583307 1.667828 -0.302148 11 6 3.216710 1.263797 -0.247057 12 6 2.903453 1.044586 1.184697 13 6 3.756183 1.955846 3.321043 14 6 2.970737 1.023543 4.016519 15 6 2.399359 -0.016214 3.289152 16 6 2.359893 -0.058546 1.866957 17 1 2.974235 0.977335 5.100907 18 1 4.430932 2.627056 3.843705 19 6 5.330681 1.659593 -1.467456 20 6 4.677742 1.287717 -2.656416 21 6 2.510727 1.330925 -1.454228 22 6 3.292169 1.202657 -2.635155 23 1 5.205114 1.219326 -3.603089 24 1 6.373773 1.959887 -1.454345 25 6 1.230886 2.015379 -1.865240 26 6 1.214524 2.072743 -3.287456 27 6 2.405529 1.348852 -3.835522 28 6 0.600105 3.088503 -4.013634 29 6 0.184610 4.233700 -3.316660 30 6 0.252964 4.213143 -1.933165 31 6 0.547021 3.036762 -1.181863 32 6 0.494157 5.389402 -1.031213 33 6 0.846582 4.801541 0.307207 34 6 0.513572 3.415938 0.250370 35 1 -0.059197 5.154378 -3.838066 36 1 0.642686 3.070143 -5.098020 37 6 1.226839 5.443331 1.473444 38 6 1.222375 4.690455 2.661520 39 6 0.603777 3.447798 2.638523 40 6 0.102058 2.836655 1.456783 41 6 0.034046 2.751129 3.837921 42 6 -1.188713 2.082953 3.289048 43 6 -1.130880 2.070391 1.866878 44 1 1.544938 5.111923 3.608774 45 1 1.487853 6.496969 1.461843 46 6 -2.375651 2.058591 4.015196 47 6 -3.574940 2.273389 3.318528 48 6 -2.357446 1.990463 1.183408 49 6 -3.523077 2.323790 1.935055 50 1 -2.338503 2.084523 5.099627 51 1 -4.493969 2.522591 3.840298 52 6 -4.420401 3.122818 1.034091 53 6 -3.735077 3.135235 -0.304296 54 6 -2.702283 2.153336 -0.248591 55 6 -4.100217 3.787140 -1.469748 56 6 -3.450844 3.407675 -2.658292 57 6 -2.684496 2.250168 -2.636606 58 6 -2.406550 1.508726 -1.455641 59 1 -3.654645 3.898721 -3.605049 60 1 -4.881859 4.540318 -1.457230 61 6 -2.359618 0.058334 -1.867106 62 6 -2.398924 0.015845 -3.289291 63 6 -2.366340 1.409422 -3.836788 64 6 -2.970452 -1.023906 -4.016570

41

65 6 -2.903300 -1.044667 -1.184768 66 6 -3.774255 -1.887121 -1.937481 67 6 -3.755980 -1.956121 -3.321036 68 1 -2.973902 -0.977789 -5.100963 69 1 -4.430753 -2.627345 -3.843640 70 6 -3.216512 -1.263759 0.247040 71 6 -4.583091 -1.667960 0.302106 72 6 -4.914812 -2.266216 -1.037046 73 6 -2.510559 -1.330730 1.454269 74 6 -3.292113 -1.202440 2.635131 75 6 -4.677677 -1.287675 2.656325 76 6 -5.330529 -1.659662 1.467364 77 1 -5.205121 -1.219241 3.602955 78 1 -6.373608 -1.960003 1.454237 79 6 -2.405530 -1.348427 3.835584 80 6 -1.230666 -2.015008 1.865452 81 6 -1.214391 -2.072164 3.287687 82 6 -0.599842 -3.087718 4.014044 83 6 -0.184169 -4.232980 3.317282 84 1 0.059746 -5.153532 3.838870 85 1 -0.642470 -3.069195 5.098427 86 6 -0.604280 -3.448130 -2.638023 87 6 -1.222805 -4.690827 -2.660729 88 6 -1.226928 -5.443590 -1.472562 89 1 -1.487911 -6.497232 -1.460841 90 1 -1.545572 -5.112426 -3.607854 91 6 1.130399 -2.070494 -1.866854 92 6 1.187801 -2.082914 -3.289048 93 6 -0.034908 -2.751434 -3.837578 94 6 2.357083 -1.990447 -1.183705 95 6 3.522569 -2.323479 -1.935705 96 6 3.574079 -2.272870 -3.319172 97 6 2.374533 -2.058240 -4.015513 98 1 2.337074 -2.084133 -5.099933 99 1 4.492989 -2.521957 -3.841208 100 6 4.420149 -3.122670 -1.035063 101 6 2.702259 -2.153420 0.248170 102 6 4.100470 -3.787283 1.468831 103 6 3.451261 -3.408027 2.657521 104 6 2.684988 -2.250476 2.636158 105 6 2.406773 -1.508892 1.455346 106 1 3.655265 -3.899219 3.604156 107 1 4.882086 -4.540484 1.456080 108 6 2.367098 -1.409854 3.836517 109 8 2.266486 -1.774445 4.990908 110 8 0.453334 6.568543 -1.323488 111 8 -2.265575 1.773859 -4.991154 112 8 -5.915532 -2.890405 -1.330762 113 8 -0.453020 -6.568250 1.324532 114 8 -2.671537 -1.080730 4.990258 115 8 -5.461369 3.677805 1.327077 116 8 0.399271 2.845329 4.992617 117 8 5.461073 -3.677474 -1.328352 118 8 -0.400488 -2.845620 -4.992208 119 8 5.915846 2.890097 1.330764 120 8 2.671298 1.080968 -4.990257 --------------------------------------------------------

Table S29. The optimized Cartesian coordinates of the [26]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ------------------------------------------------------- 1 6 -4.244898 -1.691343 3.380972 2 6 -4.144452 -1.843485 2.013215 3 6 -2.931003 -1.693075 1.261915 4 6 -1.734137 -1.802722 1.997140 5 6 -1.862510 -1.623397 3.408966

42

6 6 -3.057851 -1.486909 4.094921 7 1 -3.044523 -1.387677 5.175493 8 1 -5.202579 -1.817283 3.875716 9 6 -5.135320 -2.555336 1.153761 10 6 -4.468111 -2.713197 -0.171678 11 6 -3.304261 -1.879143 -0.170655 12 6 -4.944609 -3.389189 -1.278260 13 6 -4.252320 -3.207188 -2.483121 14 6 -3.318755 -2.184957 -2.533872 15 6 -2.926179 -1.376420 -1.425344 16 1 -4.511196 -3.739153 -3.393358 17 1 -5.827945 -4.014992 -1.198662 18 6 -2.544044 -0.024635 -2.006094 19 6 -2.453158 -0.195215 -3.423203 20 6 -2.796563 -1.597177 -3.797466 21 6 -2.820367 1.287978 -1.556078 22 6 -3.246530 2.222163 -2.555229 23 6 -3.070882 2.055101 -3.916304 24 6 -2.595279 0.817857 -4.360654 25 1 -2.534555 0.568169 -5.415784 26 1 -3.417906 2.822772 -4.601253 27 6 -4.279747 3.119492 -1.957060 28 6 -3.285411 1.836869 -0.242819 29 6 -4.416294 2.662854 -0.542429 30 6 -5.399617 3.003163 0.365712 31 6 -5.269190 2.494481 1.668121 32 6 -4.049102 1.939791 2.010750 33 6 -2.947062 1.771310 1.115301 34 1 -6.239793 3.617112 0.057062 35 1 -6.040419 2.610208 2.423144 36 6 -1.704083 1.837550 1.973358 37 6 -2.125222 1.600407 3.320173 38 6 -3.613611 1.569021 3.384363 39 6 -1.378418 1.888295 4.450875 40 6 -0.240193 2.682534 4.292049 41 6 -0.241186 5.929180 -0.660425 42 6 0.239388 5.929067 0.662104 43 6 0.306714 4.707444 1.307312 44 6 -0.031020 3.457624 0.699392 45 6 0.029926 3.457825 -0.698393 46 6 -0.308182 4.707712 -1.305958 47 1 -0.487051 6.842672 -1.192564 48 1 0.484971 6.842489 1.194495 49 6 0.682238 4.426430 2.725926 50 6 0.090597 3.084651 3.010681 51 6 -0.505197 2.572472 1.814331 52 1 0.266020 3.129304 5.142188 53 1 -1.792575 1.673685 5.431265 54 6 0.504309 2.573109 -1.813595 55 6 -0.091686 3.085439 -3.009779 56 6 -0.683692 4.426980 -2.724632 57 6 1.703383 1.838558 -1.972881 58 6 2.124482 1.601850 -3.319792 59 6 1.377527 1.889813 -4.450376 60 6 0.239111 2.683729 -4.291270 61 1 -0.267278 3.130603 -5.141251 62 1 1.791673 1.675520 -5.430839 63 6 2.946445 1.772385 -1.114944 64 6 4.048363 1.941410 -2.010451 65 6 3.612864 1.570871 -3.384112 66 6 5.268305 2.496399 -1.667815 67 6 5.398723 3.004768 -0.365276 68 6 4.415602 2.663916 0.542873

43

69 6 3.284914 1.837679 0.243152 70 1 6.238745 3.618891 -0.056554 71 1 6.039425 2.612536 -2.422886 72 6 2.820068 1.288444 1.556334 73 6 3.245989 2.222573 2.555640 74 6 4.278997 3.120238 1.957602 75 6 3.070394 2.055224 3.916690 76 6 2.595070 0.817788 4.360819 77 6 2.453185 -0.195163 3.423198 78 6 2.544101 -0.024320 2.006131 79 1 3.417207 2.822862 4.601780 80 1 2.534412 0.567909 5.415907 81 6 2.926607 -1.375902 1.425157 82 6 3.319301 -2.184552 2.533555 83 6 2.796938 -1.597110 3.797243 84 6 3.304896 -1.878285 0.170401 85 6 4.468914 -2.712101 0.171315 86 6 4.945503 -3.388185 1.277803 87 6 4.253109 -3.206556 2.482663 88 1 4.512053 -3.738634 3.392815 89 1 5.828969 -4.013795 1.198136 90 6 5.136117 -2.553917 -1.154091 91 6 4.145227 -1.841917 -2.013398 92 6 2.931702 -1.691915 -1.262130 93 6 4.245734 -1.689281 -3.381086 94 6 3.058699 -1.484716 -4.095040 95 6 1.863335 -1.621585 -3.409212 96 6 1.734912 -1.801493 -1.997456 97 1 3.045444 -1.385020 -5.175568 98 1 5.203454 -1.814954 -3.875823 99 6 0.637910 -2.090326 -4.109972 100 6 -0.023491 -2.948105 -3.084263 101 6 0.459588 -2.609961 -1.784231 102 6 -0.026398 -3.422782 -0.743944 103 6 -0.396665 -4.751625 -1.126671 104 6 -0.766883 -5.111519 -2.408887 105 6 -0.693194 -4.122032 -3.400184 106 1 -1.003911 -4.297516 -4.425004 107 1 -1.046280 -6.136456 -2.632537 108 6 0.027491 -3.423118 0.742846 109 6 0.398123 -4.752054 1.124944 110 6 0.000889 -5.657453 -0.001091 111 6 -0.637067 -2.092403 4.109508 112 6 0.024457 -2.949580 3.083391 113 6 -0.458708 -2.610924 1.783512 114 6 0.694467 -4.123469 3.398753 115 6 0.768432 -5.112464 2.406984 116 1 1.048124 -6.137429 2.630138 117 1 1.005206 -4.299359 4.423498 118 8 -6.239987 -2.955808 1.471100 119 8 -2.808887 -2.102263 -4.903707 120 8 0.332822 -1.927015 -5.274994 121 8 6.240964 -2.953922 -1.471403 122 8 2.809130 -2.102463 4.903359 123 8 4.926951 3.986531 2.512698 124 8 1.259793 5.169436 3.496251 125 8 -4.927900 3.985714 -2.512032 126 8 -1.261416 5.170065 -3.494753 127 8 4.320717 1.409069 -4.361689 128 8 0.000985 -6.873507 -0.001358 129 8 -0.332005 -1.929657 5.274618 130 8 -4.321505 1.406580 4.361796 -------------------------------------------------------

44

Table S30. The optimized Cartesian coordinates of the [28]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 -3.488041 0.760099 -4.175299 2 6 -2.625131 -0.099444 -3.519509 3 6 -2.690453 -0.491063 -2.142313 4 6 -3.650891 0.217755 -1.377908 5 6 -4.662728 0.909435 -2.133626 6 6 -4.601574 1.220421 -3.473152 7 1 -3.359112 0.916877 -5.241688 8 1 -5.435060 1.727652 -3.949021 9 6 -5.932963 0.901121 -1.363172 10 6 -5.605598 0.234138 -0.081359 11 6 -4.174616 0.154132 0.028899 12 6 -3.691146 0.102065 1.348029 13 6 -4.616604 -0.482212 2.272806 14 6 -5.972202 -0.659105 2.073640 15 6 -6.508894 -0.151617 0.886187 16 1 -7.574966 -0.065913 0.701604 17 1 -6.576455 -1.086968 2.867247 18 8 -7.021513 1.310268 -1.725147 19 6 -3.935966 -0.753087 3.555601 20 6 -2.665617 0.012417 3.474601 21 6 -2.550762 0.661045 2.196127 22 6 -2.012913 0.375089 4.639124 23 6 -1.359372 1.603554 4.649742 24 6 -1.367314 2.337718 3.480020 25 6 -1.813845 1.878781 2.192936 26 1 -0.979590 2.048485 5.562098 27 1 -2.173486 -0.209343 5.538799 28 8 -4.394750 -1.356396 4.508530 29 6 -1.364844 3.820812 3.515469 30 6 -1.883113 4.232216 2.192138 31 6 -1.793190 3.108687 1.301317 32 6 -2.404646 5.471535 1.880186 33 6 -2.949337 5.616424 0.596859 34 6 -2.640279 4.630902 -0.317114 35 6 -1.834150 3.468421 -0.055729 36 1 -2.448756 6.246771 2.638384 37 1 -3.551623 6.468096 0.297340 38 8 -1.087247 4.548991 4.453344 39 6 -3.123411 4.537751 -1.715226 40 6 -2.252605 3.520142 -2.356029 41 6 -1.297928 3.030295 -1.399030 42 8 -4.003200 5.198349 -2.238007 43 6 -2.167607 3.394169 -3.725492 44 6 -0.999607 2.841052 -4.241791 45 6 0.034806 2.597185 -3.356231 46 6 -0.018829 2.690739 -1.925485 47 1 -0.800443 2.775937 -5.306985 48 1 -2.941587 3.825839 -4.352239 49 6 1.413980 2.779322 -3.859973 50 6 2.183172 3.187121 -2.664722 51 6 1.438404 2.915827 -1.469738 52 8 1.788206 2.772905 -5.019171 53 6 3.337036 3.946397 -2.760648 54 6 3.748239 4.625456 -1.610387 55 6 3.123428 4.276216 -0.432165 56 6 2.142760 3.233583 -0.287983

45

57 1 3.795326 4.088461 -3.733779 58 1 4.489540 5.418225 -1.622980 59 6 3.143038 5.055727 0.834138 60 6 2.336197 4.264014 1.801392 61 6 2.043202 2.992773 1.190601 62 8 3.710157 6.113675 1.038154 63 6 -2.048086 -1.893962 -2.077969 64 6 -1.756604 -2.248828 -3.437856 65 6 -1.831273 -1.059759 -4.312377 66 8 -1.453224 -0.944442 -5.466312 67 6 -2.042932 -2.992940 -1.190477 68 6 -2.335616 -4.264334 -1.801077 69 6 -2.166647 -4.567996 -3.133837 70 6 -1.744405 -3.527634 -3.966906 71 1 -1.540688 -3.668643 -5.022542 72 1 -2.411039 -5.557778 -3.505772 73 6 -2.142683 -3.233484 0.288122 74 6 -3.123294 -4.276168 0.432381 75 6 -3.142461 -5.056002 -0.833760 76 8 -3.709435 -6.114044 -1.037668 77 6 -1.438489 -2.915463 1.469898 78 6 -2.183373 -3.186497 2.664840 79 6 -3.337309 -3.945707 2.760753 80 6 -3.748333 -4.625059 1.610596 81 1 -4.489631 -5.417826 1.623316 82 1 -3.795746 -4.087565 3.733844 83 6 0.018808 -2.690719 1.925682 84 6 -0.034826 -2.597333 3.356420 85 6 -1.414082 -2.778983 3.860132 86 8 -1.788320 -2.772411 5.019318 87 6 1.297828 -3.030454 1.399137 88 6 2.252391 -3.520591 2.356102 89 6 2.167366 -3.394927 3.725591 90 6 0.999479 -2.841657 4.241974 91 1 0.800287 -2.776669 5.307172 92 1 2.941260 -3.826887 4.352243 93 6 1.834131 -3.468279 0.055733 94 6 2.640353 -4.630754 0.316950 95 6 3.123235 -4.538058 1.715136 96 8 4.002884 -5.198884 2.237886 97 6 1.793226 -3.108339 -1.301279 98 6 1.883400 -4.231751 -2.192254 99 6 2.405115 -5.471046 -1.880506 100 6 2.949676 -5.616073 -0.597161 101 1 3.552027 -6.467703 -0.297658 102 1 2.449418 -6.246108 -2.638868 103 6 1.813591 -1.878349 -2.192852 104 6 1.366987 -2.337245 -3.479893 105 6 1.364988 -3.820337 -3.515528 106 8 1.087511 -4.548537 -4.453420 107 6 2.048172 1.893687 2.077975 108 6 1.756737 2.248413 3.437906 109 6 1.744847 3.527160 3.967125 110 6 2.167341 4.567522 3.134199 111 1 2.411995 5.557185 3.506277 112 1 1.541259 3.668082 5.022800 113 6 2.690379 0.490748 2.142174 114 6 2.624963 0.098894 3.519286 115 6 1.831205 1.059202 4.312291 116 8 1.453068 0.943780 5.466178 117 6 3.650956 -0.217837 1.377756 118 6 4.662795 -0.909586 2.133398 119 6 4.601539 -1.220840 3.472853

46

120 6 3.487911 -0.760683 4.174985 121 1 3.358987 -0.917560 5.241358 122 1 5.435021 -1.728047 3.948749 123 6 4.174601 -0.154075 -0.029040 124 6 5.605607 -0.234184 0.081128 125 6 5.933010 -0.901186 1.362918 126 8 7.021552 -1.310422 1.724840 127 6 3.691058 -0.101923 -1.348105 128 6 2.550533 -0.660645 -2.196110 129 6 2.665286 -0.011966 -3.474561 130 6 3.935743 0.753378 -3.555652 131 6 4.616513 0.482295 -2.272955 132 6 5.972124 0.659108 -2.073876 133 6 6.508859 0.151557 -0.886450 134 1 6.576351 1.086982 -2.867495 135 1 7.574933 0.065739 -0.701933 136 8 4.394518 1.356769 -4.508533 137 6 1.358862 -1.603048 -4.649601 138 6 2.012406 -0.374591 -4.639017 139 1 2.172907 0.209842 -5.538707 140 1 0.979051 -2.048019 -5.561929 --------------------------------------------------------

Table S31. The optimized Cartesian coordinates of the [30]circulene ketone in the ground singlet state calculated at the B3LYP/6-31(d) level of theory-------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z -------------------------------------------------------- 1 6 5.082984 2.630809 0.448697 2 6 5.347434 3.402551 -0.781778 3 6 4.233019 3.076494 -1.697079 4 6 3.448179 2.013086 -1.113306 5 6 3.739911 2.104428 0.371697 6 6 5.915206 2.604953 1.543885 7 6 5.376338 2.058168 2.706536 8 6 4.011730 1.845070 2.712200 9 6 3.084890 2.006392 1.622198 10 1 6.916897 3.017103 1.476950 11 1 5.938300 1.897024 3.620368 12 6 4.180547 3.522698 -2.996297 13 6 3.316369 2.835159 -3.841219 14 6 2.761145 1.663581 -3.362692 15 6 2.901841 1.093072 -2.052028 16 1 3.175584 3.090492 -4.885923 17 1 4.835254 4.323944 -3.323388 18 6 1.687964 2.197710 2.287757 19 6 1.874060 1.757085 3.645201 20 6 3.299826 1.539065 3.953473 21 6 1.015757 1.913166 4.714616 22 6 -0.073194 2.746530 4.534967 23 6 -0.238044 3.297936 3.280555 24 6 0.510490 2.997231 2.085255 25 1 1.322801 1.548007 5.689449 26 1 -0.709279 3.077646 5.347264 27 6 0.010660 4.030770 1.059917 28 6 -0.528125 5.114834 1.840242 29 6 -0.926520 4.601603 3.158597 30 8 3.791817 1.306504 5.046216 31 8 6.293664 4.138447 -1.002292 32 8 -1.601650 5.178166 3.993559 33 6 -0.649869 6.435020 1.463639

47

34 6 -0.143225 6.765119 0.204129 35 6 0.130369 5.704456 -0.629771 36 6 -0.026317 4.302591 -0.322464 37 6 0.703468 5.817432 -1.982336 38 6 0.521503 4.482655 -2.590440 39 6 -0.152104 3.603310 -1.664711 40 8 1.178637 6.811768 -2.504348 41 1 -1.055321 7.158250 2.163648 42 1 0.000000 7.782722 -0.144439 43 6 0.698076 4.289890 -3.939892 44 6 0.132476 3.144468 -4.484287 45 6 -0.686737 2.395222 -3.661901 46 6 -0.976323 2.604294 -2.268196 47 1 1.192712 5.054590 -4.530311 48 1 0.198281 2.880169 -5.532933 49 6 -2.397549 1.966532 -2.052028 50 6 -2.821276 1.559431 -3.362692 51 6 -1.707791 1.571092 -4.321073 52 8 -1.702659 1.138334 -5.461288 53 6 -4.113504 1.454480 -3.841219 54 6 -5.141020 1.859111 -2.996297 55 6 -4.780832 2.127655 -1.697079 56 6 -3.467473 1.979668 -1.113306 57 1 -4.264237 1.204890 -4.885923 58 1 -6.162272 2.025481 -3.323388 59 6 -5.620412 2.929738 -0.781778 60 6 -4.819839 3.086589 0.448697 61 6 -3.692444 2.186645 0.371697 62 6 -5.213559 3.820242 1.543885 63 6 -4.470595 3.626962 2.706536 64 6 -3.603743 2.551725 2.712200 65 6 -3.280031 1.668397 1.622198 66 1 -6.071336 4.481657 1.476950 67 1 -4.612021 4.194207 3.620368 68 8 -6.730832 3.381249 -1.002292 69 6 -2.747254 0.362965 2.287757 70 6 -2.458711 0.744441 3.645201 71 6 -2.982782 2.088200 3.953473 72 8 -3.027374 2.630558 5.046216 73 6 -2.850923 -1.056519 2.085255 74 6 -2.737074 -1.855120 3.280555 75 6 -2.341967 -1.436653 4.534967 76 6 -2.164729 -0.076912 4.714616 77 1 -2.002013 0.371576 5.689449 78 1 -2.310681 -2.153076 5.347264 79 6 -3.496079 -2.006153 1.059917 80 6 -4.165514 -3.014787 1.840242 81 6 -3.521845 -3.103191 3.158597 82 8 -3.683599 -3.976153 3.993559 83 6 -5.247956 -3.780313 1.463639 84 6 -5.787152 -3.506596 0.204129 85 6 -5.005388 -2.739326 -0.629771 86 6 -3.712995 -2.174086 -0.322464 87 1 -6.740035 -3.891361 -0.144439 88 1 -5.671566 -4.493060 2.163648 89 6 -5.389778 -2.299495 -1.982336 90 6 -4.142845 -1.789693 -2.590440 91 6 -3.044506 -1.933381 -1.664711 92 8 -6.488483 -2.385154 -2.504348 93 6 -4.064192 -1.540393 -3.939892 94 6 -2.789427 -1.457507 -4.484287 95 6 -1.730954 -1.792343 -3.661901 96 6 -1.767223 -2.147667 -2.268196

48

97 1 -4.973759 -1.494376 -4.530311 98 1 -2.593440 -1.268368 -5.532933 99 6 -0.504292 -3.059604 -2.052028 100 6 0.060131 -3.223013 -3.362692 101 6 -0.506710 -2.264537 -4.321073 102 8 -0.134497 -2.043713 -5.461288 103 6 2.743546 -0.456626 -2.268196 104 6 2.417692 -0.602879 -3.661901 105 6 2.214501 0.693445 -4.321073 106 8 1.837156 0.905379 -5.461288 107 6 2.656951 -1.686961 -4.484287 108 6 3.366116 -2.749497 -3.939892 109 6 3.621342 -2.692962 -2.590440 110 6 3.196610 -1.669930 -1.664711 111 1 2.395158 -1.611801 -5.532933 112 1 3.781047 -3.560214 -4.530311 113 6 3.739311 -2.128504 -0.322464 114 6 4.875020 -2.965131 -0.629771 115 6 4.686310 -3.517937 -1.982336 116 6 3.485420 -2.024617 1.059917 117 6 2.340433 -1.940713 2.085255 118 6 2.975118 -1.442816 3.280555 119 6 4.448365 -1.498412 3.158597 120 6 4.693639 -2.100047 1.840242 121 6 5.897826 -2.654707 1.463639 122 6 5.930378 -3.258523 0.204129 123 1 6.740035 -3.891361 -0.144439 124 1 6.726887 -2.665190 2.163648 125 8 5.309846 -4.426614 -2.504348 126 8 5.285248 -1.202014 3.993559 127 6 1.059290 -2.560675 2.287757 128 6 0.584650 -2.501526 3.645201 129 6 1.148972 -1.836255 4.714616 130 6 2.415162 -1.309877 4.534967 131 1 3.019959 -0.924570 5.347264 132 1 0.679213 -1.919582 5.689449 133 6 0.195141 -3.674789 1.622198 134 6 -0.407987 -4.396795 2.712200 135 6 -0.317043 -3.627266 3.953473 136 8 -0.764443 -3.937062 5.046216 137 6 -0.047468 -4.291072 0.371697 138 6 -0.263145 -5.717398 0.448697 139 6 -0.701647 -6.425195 1.543885 140 6 -0.905744 -5.685129 2.706536 141 1 -1.326279 -6.091231 3.620368 142 1 -0.845561 -7.498760 1.476950 143 6 0.019294 -3.992753 -1.113306 144 6 0.547812 -5.204149 -1.697079 145 6 0.272979 -6.332289 -0.781778 146 8 0.437169 -7.519696 -1.002292 147 6 0.797135 -4.289639 -3.841219 148 6 0.960473 -5.381809 -2.996297 149 1 1.327018 -6.349425 -3.323388 150 1 1.088653 -4.295382 -4.885923 --------------------------------------------------------

49